Phosphoric Acid → N-(4-methoxyphenyl)Glycine

Participants

Reaction Conditions

Reaction Steps

2M NaOH (aq.) (149 mL, 0.30 mol) was added dropwise to a stirred solution of ethyl 2-((4-methoxyphenyl)amino)acetate (17) (59.2 g, 0.28 mol) in EtOH/THF (300 mL/80 mL). The reaction was stirred at 40° C. for 3 h. The mixture was diluted with water (100 mL) and phosphoric acid (85% wt in water) (35.9 g, 0.31 mol) was added to pH 3. The resulting brown precipitate was collected by filtration and washed with water (100 mL) and dried under vacuum to give 2-((4-methoxyphenyl)amino)acetic acid (18) (45.5 g, 84%) as a brown solid: m/z 182 (M+H)+ (ES+); 180 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 6.78-6.64 (m, 2H), 6.55-6.44 (m, 2H), 3.74 (s, 2H), 3.64 (s, 3H).

Provenance & Evidence