Hydrochloric Acid → 3-amino-4-(methylcarbamoyl)benzoic Acid

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([NH:14][CH3:15])=[O:13])[C:5]([O:7]C)=[O:6].[OH-].[Na+].Cl>C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([NH:14][CH3:15])=[O:13])[C:5]([OH:7])=[O:6]

Participants

Procedure

A mixture of methyl 3-amino-4-(methylamino)carbonylbenzoate (0.624 g, 0.003 mol) and 1N sodium hydroxide (4.5 mol, 0.0045 mol) was stirred at room temperature for 4 h. The mixture was neutralized with concentrated hydrochloric acid and then acetic acid was added to bring the pH close to 3. The precipitate obtained was collected by filtration, washed with water, and dried under vacuum over acetone for 24 h to give 0.4 g (69%) of 3-amino-4-(methylamino)carbonylbenzoic acid as a pale yellow powder, mp 215°-217° C.