Methanol → 3-(3,4-Dimethoxyanilino)butanoic acid

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[NH:6][CH:7]([CH3:14])[CH2:8][C:9]([O:11]CC)=[O:10].[OH-].[Na+].CO>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[NH:6][CH:7]([CH3:14])[CH2:8][C:9]([OH:11])=[O:10]

Participants

Procedure

A 54-g sample of the unpurified ester product of Example 2 was combined with 17.5 g of sodium hydroxide, 550 ml of methanol and 130 ml of water, and refluxed for 1.5 hrs. The reaction mixture was cooled, concentrated under reduced pressure, diluted with water and neutralized with 6N hydrochloric acid to give an oily mixture which was extracted with chloroform. The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 48 g of an oily product. This material was used in the next step without further purification.