反应详情

温度

60 °C

A mixture of commercially available 2-chloro-5,6,7,8-tetrahydroquinoline-3-carbonitrile [CAS no 65242-27-5] (1 g, 5.19 mmol), zinc dust (activated) (602 mg, 9.2 mmol) and sodium acetate trihydrate (694 mg, 479 μl, 5.1 mmol) in acetic acid (5.19 g, 4.95 ml, 86.4 mmol) was stirred at 60° C. for 2 hours. Water (2.5 ml) was added and the mixture stirred at 60° C. for another 5 hours. After cooling to 23° C., the mixture was basified with an aqueous solution of sodium hydroxide (1M) and filtered through Celite®. The filtrate was extracted with tetrahydrofuran, the organic layers dried over sodium sulphate and the solvent evaporated leaving a yellow liquid. The crude material was purified by silica gel flash chromatography with n-heptane/ethyl acetate to give the 5,6,7,8-tetrahydroquinoline-3-carbonitrile as a white solid (433 mg, 53% yield). MS (ISP): m/z=159.1 [M+H]+.

1. stirringthe mixture stirred at 60° C. for another 5 hours
2. temperatureAfter cooling to 23° C.
3. filtrationfiltered through Celite®
4. extractionThe filtrate was extracted with tetrahydrofuran
5. dry with materialthe organic layers dried over sodium sulphate
6. customthe solvent evaporated
7. customleaving a yellow liquid
8. customThe crude material was purified by silica gel flash chromatography with n-heptane/ethyl acetate