Dimethylamine → 8-hydroxy-N,N-dimethyl-1-naphthalenesulfonamide

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Reaction Steps

Dry dimethylamine gas was passed through a solution of 1,8-naphthasultone [5.0 g, 24 mmoles, described by I. Hideo, Japanese Patent 4927, Aug. 31, 1951; Chem. Abstr., 47, 9364b (1953)] for 1.5 hr at 20°-22° C. The mixture was stirred for 20 hr. The resulting yellow crystals were collected by filtration. The filtrate was concentrated to give more crystals. The two batches of crystals were combined giving 5 g of 8-hydroxy-N,N-dimethyl-1-naphthalenesulfonamide; mp 95° C.; NMR (CDCl3) δ 2.88 (s, 6H), 7.1-8.3 (m, 6H).

Provenance & Evidence