Ammonia → HCID 20362849, compound

Participants

Reaction Steps

3.1 g of 1-tert.butylamino-3-(3-chloro-2-methyl-indol-4-yloxy)-2-propanol, 6.1 g of benzoic acid and 12 ml of hexamethyl phosphoric acid triamide are heated on a steam bath until all of the benzoic acid is dissolved. After cooling to room temperature, 2.9 g of benzoic acid anhydride are added and stirring is effected for 15 hours. The resulting clear yellow solution is poured onto ice, 250 ml of ether are added and stirring effected for 1 hour. After making the liquid alkaline with concentrated ammonia, the ether phase is separated, shaken out with tartaric acid, made alkaline while cooling with ice, with concentrated ammonia and extracted with methylene chloride. After evaporating the methylene chloride, the residual title compound is crystallised with 1 mol of malonic acid from tetrahydrofuran and ether. M.p. of hydrogen malonate form: 176°-177°.

Provenance & Evidence