Category: 1535-75-7

Synthetic Route of 1535-75-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1535-75-7, name is 2-(Trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Added the 1 -methylethyl 2-{4-[(4-bromophenyl)methyl]-1 -pi perazinyl}-3-pyrid me carboxylate (25.0 mg, 0.060 mmol), Anilines (0.120 mmol), Xphos (5.7 mg, 0.012 mmol), potassium phosphate (38.1 mg, 0.179 mmol) and palladium(ll) acetate (1.34mg, 10 mol%) in 3.0 mL Toluene in a 5 mL reaction vial, and then stirred the mixture for 30mm at room temperature under nitrogen atmosphere. The stirring was kept for 12 hr at 105 C. Pretreated a StratoSpheres PL-Thiol MP SPE column with methanol, filtered reaction mixture through column, washed with Methanol. Concentrated to give the crude product, which was dissolved in DMSO, and purified on a Gilson HPLC (XBridge 19 x 100mm 5u preparatory column), eluting at 18 mLmin with a linear gradient running from 20% to 95% acetonitrile and 0.1% aqueous NH4OH over 18 mm. The desired fractions were concentrated under a stream of nitrogen at 45 C, giving the desired product (12.83 mg, 41.7%).LCMS: mz= 515.0 [M+H], Ret. Time: 1.16 mm.

The synthetic route of 2-(Trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BOEHM, Jeffrey, Charles; DAVIS, Roderick, S.; KERNS, Jeffrey; LIN, Guoliang; MURDOCH, Robert, D.; NIE, Hong; WO2013/6596; (2013); A1;,
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Electric Literature of 1535-75-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1535-75-7, name is 2-(Trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Representative procedure for the 2-methyl-N,4-diphenylquinoline-3-carboxamide (Entry 22, Table 1): To the magnetically stirred solution of KOt-Bu (2 mmol) in THF (6 mL) at rt, was added methyl 2-methyl-4-phenylquinoline-3-carboxylate 3a (0.277 g, 1 mmol) followed by addition of aniline (0.093 mL, 1 mmol, 1 equiv) and the mixture was allow to stirred at rt until the completion of reaction (5 h, monitored by TLC) . After completion of reaction THF evaporated under rotary vacuum evaporation, crude reaction mixture was extracted with EtOAc (3 ¡Á 5 mL) and H2O (5 mL). The combined EtOAc extracts were dried (anh Na2SO4), filtered, and the filtrate was concentrated under rotary vacuum evaporation. The crude product was adsorbed on silica gel (230-400 mesh size, 500 mg), charged on to a flash chromatography column of silica-gel (230-400 mesh size, 2.5 g), and eluted with hexane-EtOAc (90:10) to obtain analytically pure 2-methyl-N,4-diphenylquinoline-3-carboxamide, 5a as white solid (0.219 g, 65%);

The synthetic route of 2-(Trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tanwar, Babita; Kumar, Asim; Yogeeswari, Perumal; Sriram, Dharmarajan; Chakraborti, Asit K.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 24; (2016); p. 5960 – 5966;,
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Electric Literature of 1535-75-7,Some common heterocyclic compound, 1535-75-7, name is 2-(Trifluoromethoxy)aniline, molecular formula is C7H6F3NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: General Procedure A: To a pressure tube containing ethyl 4,4,4- trifluoroacetoacetate (1.2 eq) and Eaton”s reagent [7.5% wt. phosphorous pentoxide p- toluenesulfonic acid solution ( 1 mL/0.3 mmol)], was added the corresponding aniline (1 eq). Then the pressure vessel was sealed and heated to 130 , and the reaction mixture was stirred overnight. After cooling to 0 C, the reaction was poured into ice water (~5 mL/1 mmol) and the solution pH was adjusted to 5 by the addition of saturated aqueous potassium carbonate. In situations when a pale yellow precipitate was formed, the solution was filtered and the residue was washed with water and cold ethanol, then dried in vacuo to yield the crude 4-hydroxyquinoline. Alternatively, the solution could be extracted with CHCl3 (20 mL x 3) and dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo to give the crude 4-hydroxyquinoline. Then the residue was purified by column chromatography using hexane”EtOAc as an eluent (30% of EtOAc) to give the desired products with yields ranging from 45% to 60%. (0217) Characterization data for compound 1 and 1a e have been reported by Kozikowski. [0140] 8-trifluoromethoxy-2-trifluoromethyl-4-quinolinol (compound 1): Yield 51%.1H NMR (DMSO-d6) 7.19 (1H, s), 7.74 (1H, apparent t, J = 8.4 Hz), 7.88 (1H, d, J = 7.2 Hz), 8.28 (1H, d, J = 8.4 Hz), 9.71 (1H, br s).13C NMR (DMSO-d6) 101.5 (q, J = 2.4 Hz), 119.9, 120.8 (q, J = 258 Hz), 122.4 (q, J = 273 Hz), 123.5, 123.7, 127.3, 128.8, 141.8 (q, 1.8 Hz), 144.5 (q, J = 36 Hz), 163.9. UVmax: 294 nm, 303 nm, 315 nm

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Trifluoromethoxy)aniline, its application will become more common.

Reference:
Patent; THE TRUSTEES OF DARTMOUTH COLLEGE; CHEUNG, Ambrose Lin Yau; NAIR-SCHAEF, Dhanalakshmi R.; WU, Jimmy; CHEN, Ji; (73 pag.)WO2017/136642; (2017); A1;,
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Electric Literature of 1535-75-7,Some common heterocyclic compound, 1535-75-7, name is 2-(Trifluoromethoxy)aniline, molecular formula is C7H6F3NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Preparation 11(2 -Trifluoromethoxy-phenvD-hydrazine hydrochlorideTo a stirred solution of hydrochloric acid (37%, 1.6 L) at 0 0C is added 2- trifluoromethoxy-phenylamine (200 g, 113 mmol) followed by water (160 mL) and additional hydrochloric acid (160 mL). The mixture is warmed to room temperature, is stirred for 20 minutes, and is cooled to -5 0C. A solution of sodium nitrite (82 g, 1.19 mmol) in water (400 mL) is added dropwise keeping the internal temperature below 0 0C. The mixture is cooled to -5 0C and a solution of tin (II) chloride dihydrate (1020 g, 4520 mmol) in of HCl (37%, 3.2 L) is added dropwise keeping the internal temperature below O0C. The mixture is warmed to room temperature, is stirred for 3 h, filtered, and washed with 6 N HCl (3L) to obtain a yellow solid that is dried under vacuum overnight The title compound (115.8 g, 54%) is obtained pink-brown solid.Preparation 12 Trifluoromethoxy-phenyl-hydrazine hydrochlorideThe title compound (115.8 g, 54%) is prepared essentially according to the preparation of (2-trifluoromethoxy-phenyl)-hydrazine hydrochloride using 2- trifluoromethoxy-phenylamine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Trifluoromethoxy)aniline, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/140183; (2007); A1;,
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Reference of 1535-75-7, The chemical industry reduces the impact on the environment during synthesis 1535-75-7, name is 2-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

Synthesis of2-chloro-5-methoxy-N-(2-(trifluoromethoxy) phenyl) pyrimidin-4-amine [0342] To a stirred solution of 2, 4-dichloro-5-methoxypyrimidine (5 g, 28.08 mmol) in tertiary butyl alcohol (35 mL) under argon atmosphere were added 2-(trifluoromethoxy) aniline (4 g, 22.47 mmol) and diisopropylethylamine (35 mL) at RT. The reaction mixture was stirred at 160 C for 48 h in a sealed tube. After completion of the reaction (monitored by TLC), the volatile components were removed in vacuo. The crude material was purified by silica gel column chromatography using 10% EtOAc:hexanes to afford 2-chloro-5-methoxy- N-(2-(trifluoromethoxy) phenyl) pyrimidin-4-amine (2 g, 22%) as a colorless syrup. 1H-NMR (CDCls, 400 MHz): delta 8.64 (d, 1H), 7.79 (s, 1H), 7.72 (br s, 1H), 7.38 (t, 1H), 7.30-7.27 (m, 1H), 7.10-7.07 (m, 1H), 4.00 (s, 3H); LC-MS: 320.3 (M+l); (column; X Select CSH C-18 (50 x 3.0 mm, 3.5 muiotaeta); RT 4.63 min. 0.05% Aq TFA: ACN; 0.80 ml/min); TLC: 15% EtOAc:hexanes {Rf. 0.3).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-(Trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1535-75-7, name is 2-(Trifluoromethoxy)aniline, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1535-75-7, SDS of cas: 1535-75-7

General procedure: To a solution of aldehyde 1 (1 mmol) in methanol, amine 2 (1 mmol), isocyanide 3 (1 mmol), and catalyst pTSIA (20 mol %) were added into a flask. Then the reaction mixture was stirred for 12-24 h at rt (monitored by TLC and LCMS until no further increase in the ratio of the desired product vs starting materials). After completion of reaction the solvent was removed under vacuum to get a crude residue. The crude residue was purified by silica gel column chromatography using (10-30%) ethylacetate-hexane to get the pure product 4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Article; Saha, Biswajit; Frett, Brendan; Wang, Yuanxiang; Li, Hong-Yu; Tetrahedron Letters; vol. 54; 19; (2013); p. 2340 – 2343;,
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Electric Literature of 1535-75-7, These common heterocyclic compound, 1535-75-7, name is 2-(Trifluoromethoxy)aniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a solution of respective anilines (1.0 eq.) in CH2Cl2 (15 mL) was added pyridine at 0 C and the mixture stirred for 5 min. Compound 4 (1.0 eq.) in CH2Cl2 (10 mL) wasadded and the mixture stirred at room temperature for 12-48 h. The mixture was diluted with CH2Cl2 (25 mL) and washed with diluted HCl and water. The organic layer wasdried over anhydrous Na2SO4 and concentrated to obtain crude was subjected to column chromatography on silica gel to yield title compounds 5.

The synthetic route of 1535-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Abbavaram, Babul Reddy A.; Reddyvari, Hymavathi R.V.; Journal of the Korean Chemical Society; vol. 57; 6; (2013); p. 731 – 737;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H6F3NO

. (2-Trifluoromethox -phenyl)-carbamic acid ethyl esterTo a solution of 2-(trifluoromethoxy)aniline (15.9 g, 0.09 mol) in DME (300 ml_) at -5 C (ice/salt bath) is added sodium hydride (3.6 g, 60% by weight, 0.09 mol) in portions. The suspension is warmed to r.t. and ethyl chloroformate (7.5 ml_, 0.08 mol) is added dropwise. The reaction mixture is stirred for 2 h at r.t. then heated to reflux for 1 .5 h. The mixture is then cooled to r.t. and water (150 ml_) is slowly added to quench the reaction. The phases are separated and the water layer is extracted with EtOAc (2×100 ml_). The combined organic layers are washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude material is purified on silica gel with EtOAc/heptanes (1 -5%) as eluent to afford the title product (1 1 .0 g, 49%) as an amber oil. 1 H NMR (300 MHz, CDCI3) delta 8.20 (d, J = 8.1 Hz, 1 H), 7.30-7.22 (m, 2H), 7.07 (app t, 1 H), 6.90 (br s, 1 H), 4.25 (q, J = 7.2 Hz, 2H), 1 .34 (t, J = 7.2 Hz, 3H);19F NMR (300 MHz, CDCI3) delta -57.32 (s, 3F);LC Rt: 2.96 min; MS 250 (M+1 , 94%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1535-75-7.

Reference:
Patent; SANOFI; CHOI-SLEDESKI, Yong Mi; LIANG, Guyan; NIEDUZAK, Thaddeus R.; POLI, Gregory B.; SHUM, Patrick Wai-Kwok; STOKLOSA, Gregory T.; ZHAO, Zhicheng; WO2011/79102; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1535-75-7, name is 2-(Trifluoromethoxy)aniline, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1535-75-7, Safety of 2-(Trifluoromethoxy)aniline

General procedure: Acetamides (1a-1x, 1ab, 1ac and 1ba-1bc). To a solution of 2-phenylacetic acid (7.0mmol), 2-(trifluoromethoxy)aniline (7.7mmol) in anhydrous CH2Cl2 (25mL) were added EDCI (1.745g, 9.1mmol) and DMAP (256.6mg, 2.1mmol). The reaction mixture was stirred at room temperature overnight, diluted with HCl (1M) aqueous solution, and extracted with CH2Cl2 (3¡Á25mL). The combined organic phase was washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous Na2SO4, and concentrated under vacuum. Purification by flash chromatography (Silica gel, petroleum ether: ethyl acetate=50: 1 as eluent) gave the corresponding 2-phenyl-N-[2-(trifluoromethoxy)phenyl]acetamide compound.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-(Trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Xiao-Jing; Zhao, Jie; Sun, Xin; Liu, Ji-Kai; Wu, Bin; Tetrahedron; vol. 73; 25; (2017); p. 3463 – 3477;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 1535-75-7, name is 2-(Trifluoromethoxy)aniline, molecular formula is C7H6F3NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. COA of Formula: C7H6F3NO

Step (1) Preparation of 2-Trifluoromethoxyphenylhydrazine Hydrochloride A solution of o-trifluoromethoxyaniline (1.77 g, 10 mmol) in cold, concentrated HCl (11.6 mL) was diazotized at -5 C. (internal temperature) with a solution of NaNO2 (0.69 g, 10 mmol) in water (11 mL). After 15-20 minutes the mixture was treated portionwise with a cold (0 C.) solution of tin (II)chloride dihydrate (4.5 g, 20 mmol) in concentrated HCl (4 mL). Stirring was continued for another 3 hours with the ice bath warming to room temperature after one hour. The suspension was recooled, basified with 50% NaOH (to pH 14) and extracted with ether. The extracts were washed with 1N NaOH, water and brine, dried (MgSO4) and acidified with an excess of ethereal HCl. Removal of the solvent in vacuo yielded the title compound as an off-white solid (2 g, 88%). It was used without further purification. NMR (DMSO-d6, 400 MHz): delta7.03 (m, 1H, ArH), 7.18 (d, J=7.5 Hz, 1H, ArH), 7.34 (m, 2H, ArH), 8.40 (s, 1H, NH). MS (EI, m/z): 197 (M)+, 77 (b.p.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1535-75-7, its application will become more common.

Reference:
Patent; American Home Products Corporation; US4960902; (1990); A;,
Ether – Wikipedia,
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