Isopropylamine → 2-(4-nitro-1H-pyrazol-1-yl)-N-(propan-2-yl)acetamide

Participants

Reaction Steps

Oxalyl chloride (29.6 g, 234 mmol) and DMF (several drops) were added to a stirred mixture of 2-(4-nitro-1H-pyrazol-1-yl)acetic acid (20 g, 117 mmol) in dichloromethane (200 mL) and stirred at room temperature for 5 h. The solvent was then removed in vacuo and the residue was diluted with THF (100 mL). This solution was added to a stirred solution of triethylamine (23.7 g, 234 mmol) and iso-propylamine (10.4 g, 176 mmol) in THF (200 mL) and the reaction was stirred at room temperature overnight. The solvent was removed in vacuo and the residue diluted with 1M hydrochloric acid to pH <4. The solid was filtered, washed with 1M hydrochloric acid and dried in a vacuum oven to afford N-isopropyl-2-(4-nitro-1H-pyrazol-1-yl)acetamide as a yellow solid (18 g, 84.8 mmol).

Provenance & Evidence