Ethyl 3-(6-quinolinyl)propanoate → Ethyl 3-(1,2,3,4-tetrahydro-6-quinolinyl)propanoate

Participants

Reaction Steps

A stirred mixture of ethyl 3-(6-quinolinyl)propanoate (0.3 g, Reference Example 3) in hydrochloric acid (3 ml, 0.1N) and 5% rhodium in carbon powder (33 mg) was hydrogenated in a 22 cm3 stainless steel pressure reactor at a pressure of 50 bars of hydrogen. After stirring for 4 hours at 25° C. a further portion of 30 mg of 5% rhodium in carbon powder (33 mg) was added and the hydrogenation was continued under a pressure of 50 bars at 25° C. for 1 hour. The reaction mixture was filtered through a pad of celite and the filter pad was washed with hydrochloric acid (3 ml, 0.1N) then with ethyl acetate (25 ml). The combined filtrate and washings were combined and the aqueous phase was decanted from the organic phase. The aqueous phase was extracted twice with ethyl acetate (25 ml) and combined with the aforementioned organic phase. The combined solutions were dried over magnesium sulfate then evaporated under reduced pressure (2.0 kPa) at 40° C. to give the title compound (0.121 g) as a brown oil.

Provenance & Evidence