Acetic Acid → N-(1,2,3,4-tetrahydroquinolin-5-yl)acetamide

Participants

Reaction Steps

A solution of 5-nitroquinoline (50 g, 0.29 mol) in 1 L acetic acid and 30 mL acetic anhydride was treated with 5% Pd/C (3 g) and shaken on a Parr apparatus under a H2 atmosphere (50.8 psi) for 10.4 hours. The reaction was then treated with PtO2 (1 g) and recharged with H2 (50.8 psi) and shaken an additional 2 hours. After removing the catalyst by filtration, the filtrate was evaporated and the residue was separated between methylene chloride and water. The aqueous layer was basified with 50% NaOH and washed with methylene chloride. The combined organic layer was dried over sodium sulfate, filtered, and evaporated. The resulting solid was crystallized from ethyl acetate (23 g, 42%).

Provenance & Evidence