Carbon Dioxide → 8-Quinolinecarboxylic acid, 5,6,7,8-tetrahydro-3-methyl-, methyl ester

Participants

Reaction Steps

A stirred solution of 3-methyl-5,6,7,8-tetrahydroquinoline (147 g., 1 m) in dry ether (700 ml.) was treated with a freshly prepared solution of butyl lithium (860 ml. of a 1.4 M solution i.e. 1.2 m) under nitrogen. The reaction mixture was stirred for an additional 15 min. The resulting 8-lithio-3-methyl-5,6,7,8-tetrahydroquinoline was treated in situ with a slow stream of dry CO2 gas which was bubbled into the reaction mixture until it became colourless. The reaction mixture was processed as described in Example 19 of our copending U.S. Ser. No. 460,265 to give methyl-3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate.

Provenance & Evidence