Uses
Methyl 2-(2-aminophenyl)acetate is used as an intermediate in organic synthesis.
Synthesis
General procedure for the synthesis of methyl (2-aminophenyl)acetate from methyl (2-nitrophenyl)acetate:
[00231] A mixture of compounds 1-2 ((2-nitrophenyl)acetic acid methyl ester, 9.75 g, 50 mmol), 10% palladium carbon catalyst (dry, 530 mg, 5 mmol) in methanol (100 mL) was subjected to a hydrogen atmosphere and stirred at room temperature overnight. Upon completion of the reaction, the reaction mixture was filtered to remove the palladium-carbon catalyst, and the filtrate was concentrated to afford compound 6-1 ((2-aminophenyl)acetic acid methyl ester, 8.02 g, yield: 97%) as a light yellow oil.
MS (ES): m/z: 166 [M + H].
1H NMR (400MHz, DMSO-d6) δ: 6.94 (m, 2H), 6.64 (d, 1H, J=8.0Hz), 6.51 (m, 1H), 4.88 (s, 2H), 3.59 (s, 3H), 3.52 (s, 2H).
References
[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 5, p. 691 - 701
[2] European Journal of Organic Chemistry, 2017, vol. 2017, # 14, p. 1889 - 1893
[3] Patent: WO2014/106238, 2014, A1. Location in patent: Paragraph 00231
[4] Patent: WO2014/106238, 2014, A1. Location in patent: Paragraph 00269; 00397
[5] Patent: WO2009/3970, 2009, A1. Location in patent: Page/Page column 42-43
