Category: 7664-66-6

Related Products of 7664-66-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 7664-66-6 name is 4-Isopropoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 4-isopropoxyaniline (151 mg) in DCM (5 mL) at 0 C was added pyridine (0.243 mL) followed by 3-carbamoyl-4-hydroxy-5-methylbenzene-1 -sulfonyl chloride (lnt-4, 250 mg). The reaction mixture was allowed to warm to RT and was stirred for 16 hr. The reaction mixture was diluted with water (30 mL) and extracted with DCM ( 2 x 50 mL). The combined DCM extracts were washed with saturated brine (25 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the crude product. The crude product was washed with diethyl ether (2 x 10 mL) and dried under vacuum to afford the titled compound (212 mg). LCMS m/z 365.09 (M+H)+. NMR (400MHz, DMSO-c/6) delta = 14.33 (br s, 1 H), 9.63 (s, 1 H), 8.74 (br s, 1 H), 8.10 (d, J = 2.2 Hz, 2H), 7.60 (d, J = 1 .3 Hz, 1 H), 6.98 – 6.91 (m, 2H), 6.80 – 6.74 (m, 2H), 4.47 (td, J=6.0, 12.1 Hz, 1 H), 2.15 (s, 3H), 1 .19 (d, J = 5.9 Hz, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Isopropoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
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Reference of 7664-66-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 7664-66-6 name is 4-Isopropoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

At room temperature, 400 mul of a 4 M solution of HCl in dioxane are added to a solution of 218 mg (1.00 mmol) of 2,5-dichloro-N-(cyclopropylmethyl)pyrimidine-4-amine and 299 mg (1.98 mmol) of 4-(isopropoxy)aniline in 12 ml of acetonitrile, and the mixture is heated at 85 C. After 16 h, the hot reaction mixture is filtered and the filtrate is allowed to cool with stirring. The product precipitated from the filtrate is filtered off and dried. This gives 130 mg (35%). logP (pH2.3): 2.11

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Isopropoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; Bayer CropScience AG; US2010/81679; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 7664-66-6,Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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.

A mixture of 3′,4′-dichloro-4-fluorobiphenyl-3-carbonitrile (173 mg, 0.650 mmol), 4-isopropoxyaniline (108 mg, 0.715 mmol), and KOtBu (154 mg, 1.375 mmol) in DMSO (4mL) was stirred at rt for 1.5h, The mixture was diluted with ethyl acetate, washed with H2O and brine, and then dried over Na2SO4. The solvent was removed and the product was purified by silica gel chromatography (eluting with hexane containing 0 to 8% ethyl acetate) followed by preparative HPLC (100 x 30 mm Luna C18 column, flow rate 42 ml permin, gradient elution starting with A:B =50:50 and ending with A:B =0: 100 [A = 10 mM NH4OAc in 5% aqueous acetonitrile; B = IO mM NH4OAc in 95% aqueous acetonitrile] over 20 min). This afforded 99 mg of 3′,4′-dichloro-4-(4-isopropoxyphenylamino)-biphenyl-3- carbonitrile which still contained some impurities according to the LC/MS but was used as such for next step. MS (ESI) m/z 397.1 (M+H).

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok, Vinayak; BATT, Douglas, G.; LIU, Qingjie; JOHNSON, Walter, L.; MASTALERZ, Harold; ZHANG, Guifen; ZIMMERMANN, Kurt; WO2010/80474; (2010); A1;,
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Reference of 7664-66-6, The chemical industry reduces the impact on the environment during synthesis 7664-66-6, name is 4-Isopropoxyaniline, I believe this compound will play a more active role in future production and life.

4-Isopropoxy-phenylamine (1.52 g, 10 mmol) in CH2Cl2 (10 mL) was slowly added to 1,1′-carbonyldiimidazole (CDI, 1.64 g, 10 mmol) in CH2Cl2 (5 mL) at 0 C. After stirring at room temperature for 1 h, 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2.05 g, 10 mmol) in CH2Cl2 (5 mL) was added and the mixture was kept stirring at room temperature overnight. It was quenched with water and extracted with CH2Cl2. The organic extracts were washed with brine, dried over Na2SO4 and evaporated. A portion of the BOC-protected product (0.35 g, 0.93 mmol) was re-dissolved in CH2Cl2 (5 mL). To this solution was added 1 mL of trifluoroacetic acid and the resulting mixture was stirred at room temperature for 1 h. The organic solvents were removed in vacuo and the crude material was neutralized with 2 M NH3 in MeOH. After evaporation of the solvents, the crude residue was purified by flash column chromatography on silica gel (5% MeOH/CH2Cl2) to afford the product as a light brown solid (250 mg, 97%). 1H NMR (CDCl3) delta 7.26 (m, 2H), 6.84 (d, J=8.70 Hz, 2H), 6.49 (br, 1H), 4.88 (m, 1H), 4.48 (sep, J=6.0 Hz, 1H), 3.12 (m, 2H), 2.83 (m, 2H), 2.04 (m, 2H), 1.71 (m, 2H), 1.31 (d, J=6.0 Hz, 6H); LC/MS (ESI) calcd for C15H23N2O3 (MH)+ 279.2, found 279.3.

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, 4-Isopropoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Baumann, Christian Andrew; Gaul, Michael David; US2006/281700; (2006); A1;,
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Ether | (C2H5)2O – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 7664-66-6 as follows. name: 4-Isopropoxyaniline

General procedure: 3-Hydroxynaphthalene-2-carboxylic acid (5.3 mmol) and the appropriate alkoxyaniline (5.3 mmol) were suspended in dry chlorobenzene (25 mL). Phosphorous trichloride (0.23 mL, 2.7 mmol) was added dropwise, and the reacting mixture was heated in the microwave reactor at maximal allowed power 500 W and 130C, using infrared flask-surface control of temperature, for 15 min. The solvent was evaporated under reduced pressure and the solid residue washed with 50 mL of 2 M HCl. The crude product was recrystallized from aqueous ethanol.

According to the analysis of related databases, 7664-66-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gonec, Tomas; Zadrazilova, Iveta; Nevin, Eoghan; Kauerova, Tereza; Pesko, Matus; Kos, Jiri; Oravec, Michal; Kollar, Peter; Coffey, Aidan; O’Mahony, Jim; Cizek, Alois; Kralova, Katarina; Jampilek, Josef; Molecules; vol. 20; 6; (2015); p. 9767 – 9787;,
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Reference of 7664-66-6, A common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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.

To a solution of 1,1′-carbonyldiimidazole (23.3 mg, 0.144 mmol) in DCM (1 mL) was added 4-isopropoxyaniline (21.7 mg, 0.144 mmol). After stirring at 0 C. for 2 h, 1-thieno[2,3-d]pyrimidin-4-yl-piperidin-4-ol (33.7 mg, 0.143 mmol), as prepared in Example 1a, was added and stirred at RT. After 2 h, DMAP (17.6 mg, 0.144 mmol) was added and stirred at 85 C. overnight. The reaction was then cooled to RT, partitioned between DCM (10 mL) and H2O (10 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. Purification by prep tlc (1:1 Hexane/EtOAc) afforded the title compound as a light green solid (8.4 mg, 14%). 1H NMR (300 MHz, CDCl3) delta 8.7 (br s, 1H), 7.44 (br m, 1H), 7.29 (m, 3H), 6.85 (m, 2H), 6.56 (br s, 1H), 5.09 (m, 1H), 4.48 (heptet, 1H), 4.17 (m, 2H), 3.75 (m, 2H), 2.11 (m, 2H), 1.87 (m, 2H), 1.31 (d, 6H). LC/MS (ESI): calcd mass 412.2, found 413.2 [M+1]+.

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baumann, Christian Andrew; Gaul, Michael David; US2006/281769; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 7664-66-6, A common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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.

To a mixture of 1-(4-chlorobenzyl)-3-(ethoxycarbonylmethyl)-6-iodoquinazoline-2,4-dion (200 mg, 0.4 mmol), palladium acetate (13.5 mg, 0.06 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (52.2 mg, 0.09 mmol), cesium carbonate (261 mg, 0.8 mmol) and dioxane (4 mL) was added 4-isopropoxyaniline (0.071 mL, 0.48 mmol) under nitrogen atmosphere, and the resulting mixture was heated at reflux for 2 hours. The reaction mixture was poured into a mixture of water (100 mL) and 5% aqueous citric acid (10 mL), and the resulting mixture was extracted with ethyl acetate (100 mL). The extract was washed by water (100 mL), dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the residue was precipitated by hexane to give 1-(4-chlorobenzyl)-3-(ethoxycarbonylmethyl)-6-(4-isopropoxyphenylamino)-quinazolin e-2,4-dion (7.7 mg, Yield: 3.7%) as yellow solid. 1H-NMR (delta ppm TMS/CDCl3): 1.28 (3H, t, J=7.2 Hz), 1.33 (6H, d, J=6.0 Hz), 4.24 (2H, q, J=7.2 Hz), 4.74 (1H, m), 4.88 (2H, s), 5.29 (2H, s), 5.61 (1H, s), 6.84 (2H, d, J=8.7 Hz), 6.91 (1H, d, J=9.0 Hz), 7.01 (2H, d, J=8.7 Hz), 7.11 (1H, dd, J=3.0, 9.0 Hz), 7.19 (2H, d, J=8.7 Hz), 7.30 (2H, d, J=8.7 Hz), 7.68 (1H, d, J=2.7 Hz).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; ENDOH, Takeshi; JIKIHARA, Sae; ASAHI, Kentaro; HORIGUCHI, Tohru; EP2604260; (2013); A1;,
Ether – Wikipedia,
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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. 7664-66-6, name is 4-Isopropoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H13NO

To a mixture of 1-(4-chlorobenzyl)-3-(ethoxycarbonylmethyl)-6-iodoquinazoline-2,4-dion (200 mg, 0.4 mmol), palladium acetate (13.5 mg, 0.06 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (52.2 mg, 0.09 mmol), cesium carbonate (261 mg, 0.8 mmol) and dioxane mL) was added 4-isopropoxyaniline (0.071 ml, 0.48 mmol) under nitrogen atmosphere, and the resulting mixture was heated at reflux for 2 hours. The reaction mixture was poured into a mixture of water (1.00 mL) and 5% aqueous citric acid (10 mL), and the resulting mixture was extracted with ethyl acetate (100 mL). The extract was washed by water (100 mL), dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the residue was precipitated by hexane to give 1-(4-chlorobenzyl)-3-(ethoxycarbonylmethyl)-6-(4-isopropoxyphenylamino)-quinazoline-2,4-dion (7.7 mg, Yield: 3.7%) as yellow solid. 1H-NMR (delta ppm TMS/CDCl3): 1.28 (3H, t, J=7.2 Hz), 1.33 (6H, d, J=6.0 Hz), 4.24 (2H, q, J=7.2 Hz), 4.74 (1H, m), 4.88 (2H, s), 5.29 (2H, s), 5.61 (1H, s), 6.84 (2H, d, J=8.7 Hz), 6.91 (1H, d, J=9.0 Hz), 7.01 (2H, d, J=8.7 Hz), 7.11 (1H, dd, J=3.0, 9.0 Hz), 7.19 (2H, d, J=8.7 Hz), 7.30 (2H, d, J=8.7 Hz), 7.68 (1H, d, J=2.7 Hz).

According to the analysis of related databases, 7664-66-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHIONOGI & CO., LTD.; Kai, Hiroyuki; Endoh, Takeshi; Jikihara, Sae; Horiguchi, Tohru; US9212130; (2015); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 7664-66-6,Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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.

Step 4: 8-Hydroxy-2-(4-isopropoxy-phenyl)-2-aza-spiror4.51decan-l-one4-Isopropoxy-phenylamine (11.3 g) was added to a solution of 4-hydroxy-l-(2-methoxy- ethyl)-cyclohexanecarboxylic acid ethyl ester (11.5 g) in toluene (361 ml). The mixture was stirred for 10 minutes at RT. Then, dimethylaluminiumchloride (0.9 M in hexane, 99 ml) was added dropwise and the reaction mixture was heated to reflux for 4 h. The mixture was then cooled to 0C, water (50 ml) was added dropwise then AcOEt (300 ml). The mixture was stirred further 30 minutes, more AcOEt was added, the layers were then separated, the organic layer was dried over MgS04, filtered and the solvent was evaporated off . The crude product was triturated with diethyl ether/heptane to give the title compound as a mixture of cis/trans isomers as brown solid (14.3 g) which was used directly in the next step. MS (m/e): 304.190 [MH+].

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HUNZIKER, Daniel; NEIDHART, Werner; WO2012/130679; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 7664-66-6, A common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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.

To a solution of compound Al (0.5 g, 065 mmol) in toluene (10 rnL) and 4- Isopropoxyaniline (202 mg, 134 mmol) was added Ti(O-iPr)4 (190 mg, 0.66 rnmol). Themixture was stirred at 120 C overnight. The mixture was quenched with H20 (50 mL) and extracted with DCM (20 mE x 3). The combined organic layer was dried over potassium carbonate, filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH == 15/1) to afford the crude products 304 and 30-2 (140 rng) as a brown solid .LC-MS: rnz 899.2 [M+H]?. To a solution of compounds 304 and 30-2 (137 mg. 015 rnmoi) in DCM (5 mE) was added DAST (24.5 rng, 0.15 mrnoi) at -78 C underN2. After stirred at -78 C for I Ii, the mixture was quenched with aqueous NaHCO3 and H20 and then extracted with DCM (30 mL x 3). i1e combined organic layer was dried over potassium carbonate, filtered and concentrated. The residue was purified by prep-HPLC to afford compound 30 (19 mg, yield14%) as yellow solid. Partial ?H NMR (CDCi3, 400 MHz): 6.93 (d, J::: Hz, 2H), 6.78-6.75 (m, 3H), 4.88 (s, 1H), 4.71-4.66 (in, 1H), 4.46-4.33 (rn, 2H), 4,32-4.29 (m, IH), 3.66-3.63 (m, 1H). 3.29-3.26 (m, 2H), 3.13-3.09 (in. 2H), 3.56-2.33 (rn, 3H); EC-MS: m/z 81.2[M+l-[[5.

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGRIMETIS, LLC; CALABRESE, Andrew; (110 pag.)WO2018/132288; (2018); A1;,
Ether – Wikipedia,
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