Lithium hydroxide, monohydrate → 2-Benzamidoisonicotinic acid

Reaction equation

[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][N:20]=1)[C:13]([O:15]CC)=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.O>[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][N:20]=1)[C:13]([OH:15])=[O:14])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Procedure

A solution of ethyl 2-benzamidoisonicotinate (1.38 g, 5.09 mmol) and lithium hydroxide monohydrate (1.07 g, 24.45 mmol) in a mixture of tetrahydrofuran (30 mL) and water (15 mL) was stirred at ambient temperature for 4 hours and the organic solvent was removed in vacuo. The aqueous solution was acidified with 10% aqueous hydrochloric acid solution until pH 7. The colorless solid was collected and dried in vacuo to give 2-benzamidoisonicotinic acid as a colorless solid (1.10 g, 89%): 1H NMR (300 MHz, DMSO-d6) δ 13.69 (s, 1H), 11.95 (s, 1H), 8.71 (s, 1H), 8.57-8.56 (m, 1H), 8.05-8.03 (m, 2H), 7.61-7.50 (m, 4H); MS (ES+) m/z 243.1 (M+1).