Acetic Acid → 6-Amino-1,3-dihydro-2H-indol-2-one

Participants

Reaction Steps

A solution of 2-(2,4-dinitrophenyl)acetic acid (1.0 g, 4.42 mmol), AcOH (10 mL), and MeOH (5 mL) was purged with Ar for 15 minutes at which time 10 wt. % Pd/C (100 mg) was added. The mixture was then purged briefly with H2 and then stirred under 1 atm of H2 overnight. The mixture was filtered through a pad of celite, the solvent removed in vacuo, and the residue purified by column chromatography (silica gel, 90:10 CH2Cl2/MeOH) to give 462 mg, 71% of a brown solid. 1H NMR (400 MHz, CD3OD) δ 6.95 (d, J=7.7 Hz, 1H), 6.37 (d, J=7.8 Hz, 1H), 6.34 (s, 1H), 3.38 (s, 2H); MS ESI 149.0 [M+H]+, calcd for [C8H8N2O+H]+149.07.

Provenance & Evidence