Benzoic acid, 5-amino-2-methoxy-, ethyl ester (9CI) synthesis

Yield:-

Reaction Conditions:

with hydrogen;palladium over charcoal in ethyl acetate; under 760.051 Torr; for 4 h;

Steps:

132

To a solution of ethyl 2-methoxy-5-nitrobenzoate (1.6g) in 20ml EtOAc was added lOOmg of palladium on carbon, the resulting solution treated with 1 atmosphere of Hydrogen gas for 4 hour. The reaction mixture was filtrated over celite, concentrated in vacuo and chromatographed on silica gel using an ISCO single channel system (Hexane/EtOAc = 9/1 to 1/9) to give product ethyl 5-amino-2-methoxybenzoate. 1H NMR (CDCl3, 500 MHz) δ 8.7.142-7.137 (m, IH), 6.83-6.79 (m, 2H), 4.36-4.32 (q. 2H), 3.83 (s, 3H), 1.38-1.36 (t, 3H).

References:

WO2006/14918,2006,A2 Location in patent:Page/Page column 81