Ethyl 3-acetamido-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate → 3-Amino-3,4-dihydroquinolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

3-(N-Acetylamino)-3-carboethoxy-1,2,3,4-tetrahydroquinolin-2-one (0.75 g, 100M %) was suspended in 6N HCl (25 mL) and the mixture was heated to 100° C. for 3 hours. The reaction was cooled, rotoevaporated to a residue and then partitioned between water and ethyl acetate. The water was extracted with ethyl acetate (3×) and the combined ethyl acetate extracts were then washed with water (3×) and then brine (1×). Treatment with MgSO4 followed by rotoevaporation yielded 3-(R,S)-amino-1,2,3,4-tetrahydroquinolin-2-one (72% yield).

Provenance & Evidence