Methanol → HCID 178419599, compound

Participants

Reaction Conditions

Reaction Steps

Boron tribromide (25.0 grams, 99.8 mmol) was added dropwise to a solution of 2.14 grams 4-carbomethoxyethyl-3-hydroxy-6,7,8-trimethoxy-1-methylisoquinoline (6.38 mmol) (Compound J) in 35 ml methylene chloride cooled to -50° C. (in a dry ice-acetone slush bath) under a nitrogen atmosphere. A gummy residue formed immediately. The reaction mixture was warmed to room temperature, stirred for 4 hours and then was cooled to 0°-5° C. Methanol (30 ml) was added dropwise over a 45 minute period and a clear solution was obtained. The solvent was removed in vacuo to provide a brown solid residue which was triturated with ether for 64 hours and then filtered. The solid was washed with ether and dried in vacuo at room temperature to provide 2.14 grams of Compound N (89.7% yield) having a melting point of 172° to 174° C.

Provenance & Evidence