Acetic Acid → 5'-Chlorospiro(cyclopentane-1,3'-indoline)-2-one

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Reaction Steps

Spiro(cyclopentane-1,3'-indoline)-2'-one (18.7 g; 0.10 moles) is dissolved in acetic acid (50 ml) containing 100 mg of ferrichloride hexahydrate, cooled in ice-water and drop-wise treated under agitation with a solution of clorine in acetic acid (82 ml of a solution containing 7.8 g per 100 ml). After the addition air is blown through the solution to eliminate a possible excess of clorine as well as hydrogen cloride. The crystallized product (8.7 g) is sucked off and the filtrate is concentrated in vacuum, upon which an additional product quantity (7.3 g) is obtained. After recrystallization from ethanol the substance melts at 201° - 202° C.

Provenance & Evidence