Sodium hydride → N-[3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of methanesulfonamide (2.6 g, 27.2 mmol) in N,N-dimethylformamide (5 mL) was added sodium hydride (1.1 g, 27.5 mmol). The resulting mixture was stirred at 25° C. for 1 h. A solution of 3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (1.79 g, 5.5 mmol) and 1,1′-carbonyldiimidazole (1.78 g, 11 mmol) in N,N-dimethylformamide (5 mL) was stirred at 70° C. for 1 h. Then the above suspension of methanesulfonamide and sodium hydride in N,N-dimethylformamide was added and the mixture was allowed to stir at 25° C. for 1 h. The reaction mixture was extracted with ethyl acetate (2×100 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford N-[3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide (2 g, 90%) as a brown solid which was used for next step without further purification: LC/MS m/e calcd for C19H21N3O5S (M+H)+: 404.46, observed: 404.1.

Provenance & Evidence