Category: 1484-26-0

1484-26-0, A common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

B. 3-Benzyloxyphenyl isocyante. To a stirred solution of 3-benzyloxyaniline (507 mg, 2.54 mmol) in toluene (5 mL) containing TEA (740 muL, 5.34 mmol) was added 20percent phosgene in toluene (1.5 mL, 2.83 mmol). The reaction was stirred for 20 h at rt. The organic layer was washed with H2O (20 mL), dried (MgSO4) and concentrated to give a clear brown oil (497 mg, 87percent). The material was used in subsequent steps without charaterization.

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Butler, Christopher R.; Edwards, James P.; Fourie, Anne M.; Grice, Cheryl A.; Karlsson, Lars; Savall, Brad M.; Tays, Kevin L.; Wei, Jianmei; US2006/223792; (2006); A1;,
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Application of 1484-26-0, These common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, 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 stirred solutionof 3-(benzyloxy)aniline 10b (1.0 equiv.) in ethylformate (3 mL),catalytic amount of pTsOH monohydrate was added. The reactionmixture was stirred at rt for 3 days and the resulting mixture wasextracted with ethyl acetate. Organic layers were collected, washedwith water and brine, dried over anhydrous MgSO4 and evaporatedgiving the product 11b as white solid in 80percent yield.xNMR: mixture of two rotamers (approx. 1:1) 1H (600 MHz,CDCl3): d 8.67 (d, J 10.0 Hz, 1H), 8.32 (s, 1H), 7.97e7.67 (m, 22H),5.05 (s, 2H), 5.03 (s, 2H).

Statistics shows that 3-Benzyloxyaniline is playing an increasingly important role. we look forward to future research findings about 1484-26-0.

Reference:
Article; Surmiak, Ewa; Neochoritis, Constantinos G.; Musielak, Bogdan; Twarda-Clapa, Aleksandra; Kurpiewska, Katarzyna; Dubin, Grzegorz; Camacho, Carlos; Holak, Tad A.; Doemling, Alexander; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 384 – 407;,
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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. 1484-26-0, name is 3-Benzyloxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 1484-26-0

3-Benzyloxyaniline (80 mg, 0.40 mmol) was dissolved in DCM and cooled to 0 °C. Bromoacetyl bromide (2 equiv, 70 lL) and Et3N (5 equiv, 280 lL) were added slowly and the mixture was stirred at 0 °C for 6 h. 2,5-Dimethoxybenzylamine (2.5 equiv, 151 lL)was added at 0 °C and the mixture was allowed to warm over 16 h of stirring. Boc2O (6 equiv, 524 mg) was added along with 2 addition equiv of Et3N and DMAP (0.2 equiv, 10 mg) and the mixture was stirred for 1 h at rt. The reaction mixture was diluted with satd NaHCO3 and extracted with DCM. The crude product was purified by pTLC with 30percent EtOAc in hexane to afford N-Boc-33 as a colorlessoil (49 mg, 24percent).

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bremer, Paul T.; Hixon, Mark S.; Janda, Kim D.; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 3971 – 3981;,
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Related Products of 1484-26-0, 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. 1484-26-0, name is 3-Benzyloxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 4-bromobenzoate (49 mg, 0.23 mmol) and 3 -benzyloxy aniline (50 mg, 0.25 mmol) are dissolved in dry dioxane (1 mL). Pd2(dba)3 (21 mg, 0.023 mmol), (^Bu)3PHBF4 (13 mg, 0.046 mmol) and cesium carbonate (149 mg, 0.46 mmol) are added and the mixture is degassed with bubbling Ar for 15 min. The vessel is sealed and heated at 120°C for 72 h. LiOH (IN, 0.5 mL) is added and heated at 90°C for 1 h, then is cooled, quenched with IN HCl (5 mL) and extracted into EtOAc (10 mL). The organic layer is dried (MgSO4), filtered, concentrated and purified on reverse phase HPLC (H2O/MeCN gradient) to afford the title compound 4-(3-(benzyloxy)phenylamino)benzoic acid (Hl). 1H-NMR (400 MHz, CDC13) delta = 7.96 (d, J = 8.8 Hz, 2H), 7.40 (m, 5H), 7.25 (t, J = 8.0 Hz, IH), 6.97 (d, J = 8.8 Hz, 2H), 6.81 (t, J = 2.4 Hz, IH), 6.76 (ddd, J = 1.2, 2.4, 8.0 Hz, IH), 6.71 (dd, J = 1.8 Hz, 8.0 Hz, IH), 5.07 (s, 2H). MS calcd. for C20H18NO3 (M+H+) 320.1, found 320.2.

The synthetic route of 3-Benzyloxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2008/121570; (2008); A1;,
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Application of 1484-26-0,Some common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

N-(3-Benzyloxy-phenyl)guanidine: To a suspension of 3-benzyloxyphenylamine (20.0 g, 100.35 mmol) in 1,4-dioxane (150 mL) was added cyanamide (7.39 g, 175.95 mmol) followed by 4M HCl in 1,4-dioxane (44 ml, 176.00 mmol). The resulting suspension was heated at 80° C. overnight then cooled to ambient temperature and 6N NaOH (35 ml, 210.00 mmol) was added. The volume of solution was reduced to 50 ml in vacuo and the resulting precipitate was collected by filtration. The solid product was dried under vacuum overnight to afford23.8 g in 98.4percent yield. 1H NMR (MeOH-d4) delta 6.4-7.5 (m, 9H), 5.1 (s, 2H)

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cao, Jingrong; Green, Jeremy; Moon, Young-Choon; Wang, Jian; Ledeboer, Mark; Harrington, Edmund; Gao, Huai; US2003/96816; (2003); A1;,
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1484-26-0, name is 3-Benzyloxyaniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 1484-26-0

Phenyl [3-(benzyloxy)phenyl]carbamate; To a stirred solution of 3-benzyloxyaniline (0.999 g, 5.01 mmol) in DCM (10 piL) was added pyridine (1.22 ml, 15.03 mmol) and phenyl chloroformate (0.68 ml, 5.51 mmol) dropwise (Exotherm.). The reaction was then allowed to stir at room temperature for 2 hours. The reaction mixture was then partitioned between DCM and IM HCl, extracted twice, combined organics passed through phase separating cartridge and filtrate evaporated to dryness to give an orange solid. This was then triturated in 10percent ethyl acetate/ hexanes, filtered and dried to give the product, phenyl [3-(benzyloxy)phenyl]carbamate, as beige solid (1.209 g, 3.78 mmol, 75percent yield).

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/67401; (2006); A1;,
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Synthetic Route of 1484-26-0, A common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

A mixture of triethyl orthoformate (92 ML, 0.55 mol) and 2, 2-DIMETHYL- [1, 3] – dioxane-4,6-dione (75.3 g, 0.522 mol) (Meldrum’s acid) was heated at 55 °C for 90 minutes and then cooled to 45 °C. A solution of 3-benzyloxyaniline (100.2 g, 0.5029 mol) in methanol (200 mL) was slowly added to the reaction over a period 45 minutes while maintaining the reaction temperature below 50 °C. The reaction was then heated at 45 °C for one hour, allowed to cool to room temperature, and stirred overnight. The reaction mixture was cooled to 1 °C, and the product was isolated by filtration and washed with cold ethanol (-400 mL) until the filtrate was colorless. 5-F [ (3- Benzyloxy) phenylimino] METHYL}-2, 2-dimethyl- [1, 3]-dioxane-4, 6-dione (170.65 g) was isolated as a tan, powdery solid. 1H NMR (300MHZ, DMSO-D6) : 8 11. 21 (d, J= 14. 2 Hz, 1H), 8.61 (d, J= 14.2 Hz, 1H), 7.49-7. 30 (m, 7H), 7.12 (dd, J= 8.1, 1.96 Hz, 1H), 6.91 (dd, J= 8.4, 2.1 Hz, 1H), 5.16 (s, 2H), 1. 68 (s, 6H).

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2005/20999; (2005); A1;,
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1484-26-0, name is 3-Benzyloxyaniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C13H13NO

4-Chloro-6-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7Hpyrrolo-[2,3-d]pyrimidine [8] (600 mg, 1.46 mmol) and 3-(benzyloxy)aniline (585 mg, 2.94 mmol) were dissolved in nbutanol(12 mL) under an N2-atmosphere. The reaction mixturewas agitated at 100 °C for 6.5 hours. Following work-up asdescribed in Section 2.4.1, the crude product was purified twiceby silica-gel column chromatography (n-pentane/THF, 9/2, Rf = 0.37). Drying gave 661 mg(1.15 mmol, 79percent) of a orange solid.

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reiers°lmoen, Ann Christin; Han, Jin; Sundby, Eirik; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 562 – 578;,
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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. 1484-26-0, name is 3-Benzyloxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1484-26-0

A suspension of 2-chloro-5-bromopyrimidine (300 mg, 1.55 mol), 3-benzyloxyaniline (680 mg, 3.41 mmol), tpi’5′(dibenzylideneacetone)palladium(0) (56 mg, 61.1 mumol), 4,5-fos(diphenylphosphino)-9,9-dimethylxanthene (71 mg, 122.7 mumol) and cesium carbonate (1.21 g, 3.72 mmol) in degassed 1,4-dioxan (7 mL) was heated at 80°C for 4 days. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water, 0.5 M hydrochloric acid and brine. The organic phase was dried (MgSO4) and the solvent removed under reduced pressure to give a thick orange- brown oil. The crude product was purified by column chromatography on silica gel eluting with 1:3 ethyl acetate/petroleum ether to afford the title compound as an off- white solid (203 mg, 28 percent). deltaH (4-DMSO, 400 MHz): 5.08 (2 H, s), 5.10 (2 H, s), 6.42-6.50 (3 H, m), 6.58 (1 H, d), 7.11 (1 H, t), 7.20 (1 H, t), 7.30-7.50 (11 H, m), 7.62 (1 H, s), 7.91 (1 H, s), 8.38 (2 H, s) and 9.53 (1 H, s).LCMS (ES+): 475 (MH+, 100 percent).

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 1484-26-0.

Reference:
Patent; SENEXIS LIMITED; WO2007/125351; (2007); A1;,
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These common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, 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. SDS of cas: 1484-26-0

General Procedure: Aniline (10, 10 mmol), 2-chloroethanol (2 mL), CaCO3 (2.00 g, 20 mmol) and KI (10percent mmol) were added to 14 mL water and refluxed for 8 h. After filtration, the filtrate was extracted with EtOAc (14 mL.x.3), and the combined organic layers were washed with saturated NaCl (14 mL.x.2), dried over anhydrous Na2SO4, filtered and concentrated. Column chromatography afforded the desired product 11.

The synthetic route of 3-Benzyloxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Song-Wen; Sun, Qi; Ge, Ze-Mei; Wang, Xin; Ye, Jia; Li, Run-Tao; Bioorganic and Medicinal Chemistry Letters; vol. 21; 3; (2011); p. 940 – 943;,
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