Carbon Dioxide → HCID 12278957, compound

Participants

Reaction Steps

A solution of 5,6,7,8-tetrahydroquinoline (14 g.) in dry ether (100 ml.) was added dropwise over 1/2 hour to an ethereal solution of phenyl lithium (prepared from bromobenzene (42 g.) and lithium (3.7 g.) in dry ether (300 ml.) and the reaction mixture stirred at room temperature for a further one hour. The cooled reaction mixture containing 8-lithio-5,6,7,8-tetrahydroquinoline was saturated with dry CO2 gas, evaporated in vacuo and the residue treated with methanol previously saturated with dry HCl (500 ml.) giving methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate as described in our copending U.S. Ser. No. 460,265.

Provenance & Evidence