Sodium Hydroxide → 2-iodo-1,4-benzenediamine

Participants

Reaction Steps

A mixture of concentrated hydrochloric acid (150 ml) and 2-iodo-4-nitroaniline (30.0 g) is stirred and warmed to 45°-50° C. A solution of stannous chloride dihydrate (90.0 g) in concentrated hydrochloric acid (110 ml) is added while maintaining the reaction temperature at 65°-70° C. After the addition is completed, the mixture is cooled in an ice bath and 50% sodium hydroxide (250 ml) is added slowly. The mixture is filtered and the isolated damp solid is stirred in 600 ml water at reflux. The solution is decolorized with charcoal, filtered and cooled to afford 5.55 g of title compound, m.p. 95°-99° C.

Provenance & Evidence