Bicyclo(2.2.1)heptan-2-one → HCID 21960027, compound

Participants

Reaction Conditions

Reaction Steps

Anthranilonitrile (2.40 g) was mixed together with norcamphor (4.40 g) and then 4.0 g of freshly fused ZnCl2 was added and the reaction mixture was heated at 120° C. After 1.5 hours it became so thick that it could not be stirred, so 10 ml of 1,2-dichloroethane was added and the reaction mixture was refluxed for 1 hour. At the end of this time, 40 ml of 10% NaOH was added and the mixture was stirred overnight. It was then extracted several times with 2-butanone which gave a crude product that was purified by flash chromatography (EtOAc, then 5% Et2NH/EtOAc) to give 3.04 g of foam. Recrystallization from CH2Cl2 /pentane gave 2.30 g of analytically pure product, m.p. 186°-188°.

Provenance & Evidence