Sodium hydride → HCID 53689583, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-3-(4-nitrobenzoyl)aminopyridine (1.93 g) in N,N-dimethylformamide (13 ml) was added sodium hydride (60 % in oil, 585 mg) and the solution was stirred at 0° C. for ten minutes. 3-Dimethylaminopropyl chloride hydrochloride (1.16 g) was added to the solution and the mixture was stirred for 3 hours at 150° C. The solution was diluted with ethyl acetate and the solution was washed with successively with water, saturated aqueous sodium hydrogen carbonate and brine. The organic phase was dried over sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (80 g, ethyl acetate:n-hexane =1:3) to give 1-(4-nitrobenzoyl)-5-methyl-2,3,4,5-tetrahydropyrido [3,2 -b][1,4]diazepine (450 mg).

Provenance & Evidence