Hydrochloric Acid → 5'-Chloro-spiro(cyclopentane-1,1'-indan)-3'-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 5'-amino-spiro(cyclopentane-1,1'-indan)-3'-one (20.1 g; 0.1 mole), 23% hydrochloric acid (35 ml), water (76 ml) and ice (3 g) is diazotised at about +5° C. with a solution of sodium nitrate (11 g) in water (25 ml). The clear solution is added to an ice cooled solution of copper(I)chloride(15 g) in 23% hydrochloric acid (150 ml) and water (60 ml). After agitation for 2.5 hours the mixture is heated to 100° C. for a short while and is then allowed to cool. The brown precipitate is sucked off and thoroughly washed with water. Crude yield 20 g (90%). The crude product is purified by distillation in vacuum, bp. 135°-136° C./1,5 mm Hg. A sample is crystallized from n-hexane and then melts at 54° C. The oxime melts at 140° C.

Provenance & Evidence