4-Chloroanisole → HCID 54188056, compound

Participants

Reaction Steps

γ-Phenylacetoacetic acid ethyl ester was converted into 3-amino-4-phenylbutyric acid ethyl ester (M.P. of hydrogen oxalate 151°-153°). Further reaction with p-anisolyl chloride gave 3-p-methoxybenzamido-4-phenylbutyric acid ethyl ester (M.P. 102°-104°). A Bischler-Napieralski reaction (boiling with phosphorus oxychloride) gave 3,4-dihydro-1-p-methoxyphenyl-3-isoquinolinylacetic acid ethyl ester. Hydrogenation using a palladium/charcoal (10% w /w) gave cis-1-p-methoxyphenyl-1,2,3,4-tetrahydro-3-isoquinolinylacetic acid ethyl ester.

Provenance & Evidence