Hydrochloric Acid → Acetamide, N-3-quinolinyl-

Participants

Reaction Steps

Acetyl chloride (410 mg, 5.2 mmol) and triethylamine (620 mg, 6.2 mmol) were added to a solution of 3-aminoquinoline (710 mg, 4.9 mmol) in dichloromethane (50 ml) and the mixture was stirred at room temperature for 18 h. Chloroform (100 ml) was added, the mixture acidified with 1N hydrochloric acid (50 ml) and the phases separated. The aqueous phase was basified with 1N sodium hydroxide solution and extracted with chloroform/IPA (85:15, 175 ml). The organic extract was washed with water, brine, dried and reduced to afford 3-acetamidoquinoline (780 mg, 84%) as a yellow solid.

Provenance & Evidence