Hydrochloric Acid → 2-Amino-4-(benzyloxy)benzoic acid

Reaction equation

C([O:8][C:9](=[O:28])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][C:11]=1[NH:24]C(=O)C)C1C=CC=CC=1.[OH-].[Na+].Cl>CCO>[NH2:24][C:11]1[CH:12]=[C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:15][C:10]=1[C:9]([OH:28])=[O:8]

Participants

Procedure

A suspension of 1.87 g (4.98 mmol) of 2-acetylamino-4-benzyloxy-benzoic acid benzyl ester in EtOH (20 ml) was treated with 1N NaOH (20–30 ml) and stirred at 95° C.–130° C. (oil bath temperature) until completion of the reaction according to TLC and NMR analysis (reaction time about 34 h). The reaction mixture was cooled to RT, brought to pH 6 on addition of 1N aqueous HCl, the precipitate that formed was filtered off by suction and dried in a high vacuum to give 1.19 g (91.7%) of the desired 2-amino-4-benzyloxy-benzoic acid as an off-white solid. ISP mass spectrum, m/e: 242.2 (M+1 calculated for C14H13NO3: 242).