Ethyl Acetate → 3-(N-Propyl)amino-1,2,3,4-tetrahydroquinoline

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To a ice-cooled solution of 3.2 g (15.6 mmol) 3-(N-propionyl)amino-1,2,3,4-tetrahydroquinoline in 50 ml dry diethyl ether and 80 ml dry tetrahydrofurane was 3.0 g (79 mmol) lithium aluminum hydride added. The mixture was gently heated to reflux and kept that way for 5 days. Ethyl acetate (4.5 ml), 3.0 ml water,3.0 ml 15% sodium hydroxide and 9 ml water was added consecutively. The precipitate appearing after 5 minutes was filtered off and washed with diethyl ether. Evaporation of the etheric solution yielded 2.66 g (89%) of the desired product: 13C NMR 0 d 11 (76), 23.46, 33.71, 46.41, 48.98, 50.43, 113.79, 117.29, 119.37, 126.87, 130.06, 144.09; MS m/e 190 (M+, 17), 132 (100), 130 (32), 72 (22), 118 (17), 131 (17).

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