Formic Acid → HCID 178423431, compound

Participants

Reaction Steps

N-benzyl-5-(hydrazinyl(imino)methyl)-3-methylthiophene-2-carboxamide (0.65 g, 2.24 mmol) in formic acid (20 mL) was stirred at reflux for 2 h. The reaction mixture was allowed to cool to ambient temperature, and then was concentrated in vacuo. The residue was dissolved in saturated aqueous sodium bicarbonate solution (50 mL) and extracted with 5% methanol in dichloromethane (3×75 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with dichloromethane in hexanes to afford the title compound as a light yellow solid (0.56 g, 84%): 1H NMR (300 MHz, CDCl3) δ 8.23 (s, 1H), 7.48 (s, 1H), 7.39-7.30 (m, 5H), 6.14 (br s, 1H), 4.63 (d, J=5.4 Hz, 2H), 2.54 (s, 3H); MS (ES+) m/z 299.2 (M+1).

Provenance & Evidence