Hydrochloric Acid → 5,6,7,8-Tetrahydro-4-methyl-8-(3,4-dimethylbenzoyl)quinoline hydrochloride

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Reaction Steps

After 0.5h, a 1.36M solution of butyl lithium (11.2ml, 0.017m) was added at 0.° C. and the mixture stirred at this temperature for a further 0.5h. A solution of 3,4-dimethylbenzonitrile (2.6g, 0.02m) in THF (20ml) was added rapidly and after 0.5h a solution of 2M hydrochloric acid (40ml) was added and the aqueous phase separated. This was basified with solid potassium carbonate and the mixture extracted with ether. The mixture was purified by chromatography on silica using ether as eluant. The isolated product was dissolved in ether and acidified with ethereal HCl to give 5,6,7,8-tetrahydro-4-methyl-8-(3,4-dimethylbenzoyl)quinoline hydrochloride (2.5g, 53%) m.p. 237°-9° C. (Found; C,72.25; H, 7.0;N, 4.4 C19H21NO.HCl requires C, 71.8; H, 7.1; N, 4.3%).

Provenance & Evidence