4-Toluenesulfonyl chloride → HCID 178427409, compound

Participants

Reaction Steps

A solution of p-toluenesulphonyl chloride (7.0 g.) in ether (30 ml.) was added to a stirred solution of 6-amino-4-hydroxycinnolin-3-yl carboxylic acid (1.025 g.) in N-sodium hydroxide solution (15 ml.). The heterogeneous mixture was stirred vigorously for 16 hours. The aqueous phase was separated, washed with ether (2 × 25 ml.), and acidified to pH 2 with 5N-hydrochloric acid. The solid which separated was filtered off, washed with water and dried as much as possible on the filter. The product was purified by chromatography on a silica column (30 g., Kieselgel 60), eluted with a mixture of ethanol (15 parts by volume), chloroform (85 parts by volume) and formic acid (1 parts by volume), to give 4-hydroxy-6-(p-toluenesulphonylamino)cinnolin-3-yl carboxylic acid, m.p. 272°-273° C. EXAMPLE 16

Provenance & Evidence