Aluminum(III) Chloride → HCID 172035639, compound

Participants

Reaction Conditions

Reaction Steps

The carboxylic acid from example 3 (150 mg, 0.25 mmole), was converted to its acid chloride using the same procedure as described. The acid chloride was suspended in dry dichloromethane, (10 ml), and the mixture stirred at -20° C. Aluminium chloride, (127 mg, 0.95 mmole), was added portionwise to the mixture and stirring continued for 2 hours at -20° C. The reaction was warmed to 0° C. over 1 hour, then stirred for 2 hours at 0° C., then quenched with dilute hydrochloric acid, (20 ml). After standing overnight the mixture was decanted and the residual orange gum was washed with a little water and triturated with hot methanol. Filtration of the cooled mixture gave 20 mg (16%) of the title compound as its hydrochloride. The free base was obtained by suspending the solid in water, neutralizing to pH 7 with dilute sodium hydrogen carbonate solution and filtering off the pale orange solid. After drying in vacuo 14 mg (12%) of the title compound was isolated.

Provenance & Evidence