4'-(Bromomethyl)-2-cyanobiphenyl → HCID 18954308, compound

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Reaction Steps

12.5 g of potassium tert-butoxide are added at 20° to a solution of 20.3g or 7-ethyl-1,2,3,4-tetrahydro-4,4-dimethyl-2-oxoquinoline [mip. 120°; obtainable by reaction of m-ethylaniline with 3,3-dimethylacryloyl chloride in toluene/methylene chloride to give N-(3,3-dimethylacryloyl)-m-ethylaniline (m.p. 90°) and cyclisation with AlCl3 at 60°-100°]in 700 ml of DMF. The mixure is stirred for 45 minutes, a solution of 30.5g of 4-bromomethyl-2'-cyanobiphenyl in 300 ml of DMF is then added dropwise and the mixture is stirred overnight, evaporated and worked up in conventional manner to give 1-(2'-cyanobiphenyl-4-ylmethyl)-7-ethyl-1,2,3,4-tetrahydro-4,4-dimethyl-2-oxoquinol ine, m.p. 171°-172°.

Provenance & Evidence