Anthranilic Acid → 2-(Isopropylamino)benzoic acid

Reaction equation

[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11](O)(=O)[C:12]1C(=CC=C[CH:20]=1)C(O)=O.[BH4-].[Na+]>CC(C)=O>[CH:12]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9])([CH3:20])[CH3:11]

Participants

Procedure

To stirred mixture of 2.7 g. of anthranilic acid and 5.4 g. of phthalic acid in 23 ml. of acetone is added 0.7 g. of powdered sodium borohydride over a period of 30 minutes at 20° C.-30° C. The resulting slurry is then stirred at 35°-40° C. for 4 hours, diluted with 25 ml. of chloroform and filtered. The filtrate is concentrated in vacuo and the residue dissolved in 20 ml. of chloroform and treated with 30 ml. of hexane, filtered and the filtrate concentrated in vacuo to obtain a crude solid product which is recrystallized 5 times from cyclohexane to obtain (second crop of fifth recrystallization) N-isopropylanthranilic acid, m.p. 109°-109.5° C.