Sodium hydride → HCID 19039999, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% dispersion in oil; 160 mg) was added to a solution of 5-dimethylamino-1-naphthalenesulphonamide (500 mg) in N,N-dimethylformamide (30 ml). When evolution of hydrogen ceased, 2-chloro-5-nitropyridine (317 mg) was added and the solution was heated at 95° C. for 18 hours. Volatile material was removed by evaporation and water (50 ml) was added to the residue. The mixture was extracted with ethyl acetate (20 ml), and the aqueous layer was neutralised with 0.05M aqueous acetic acid (40 ml) and extracted with ethyl acetate (3×25 ml). The extracts were washed with water (20 ml) and saturated sodium chloride solution (20 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by elution with dichloromethane through a silica gel Mega Bond Elut column. The resulting foam was triturated with ether/hexane (1:1 v/v) to give 5(dimethylamino)-N-(5-nitro-2-Pyridyl)-1-naphthalenesulphonamide (60 mg), m.p. 196° C.; mass spectrum (+ve FAB, methanol/NBA): 373 (M+H)+.

Provenance & Evidence