Carbon Dioxide → HCID 21314201, compound

Participants

Reaction Steps

A solution of 4-methyl-5,6,7,8-tetrahydroquinoline (5.83 g., 0.04 mole) in dry benzene (40 ml.) was cooled to 0° and to the stirred solution was added dropwise a 15% w/w solution of butyl lithium in hexane (17.5 ml., 0.04 mole) under an atmosphere of nitrogen. The red reaction mixture of 8-lithio-4-methyl-5,6,7,8-tetrahydroquinoline was stirred at 0° for a further 30 minutes. It can then be treated with carbon dioxide followed by methanolic HCl to obtain methyl-4-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate which can be converted to 4-methyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide by the procedures described in copending U.S. Ser. No. 460,265.

Provenance & Evidence