Triethylamine → HCID 22417798, compound

Participants

Reaction Steps

To a suspension of 6-amino-4-(p-cyclohexylmethoxyanilino) -2-phenylquinoline hydrochloride (0.21 g, 0.5 mmol) in anhydrous THF (10 ml) at 0° C. was added methanesulfonyl chloride (69 mg, 0.6 mmol) followed by addition of triethylamine (61 mg, 0.6 mmol). The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. The solvent was removed by rotary evaporation and the residue partitioned between ethyl acetate (EtOAc) and 1M hydrochloric acid. The layers were separated, the organic layer was washed with saturated sodium bicarbonate and dried (Na2SO4) and the solvent was removed by rotary evaporation. The crude material was dissolved in warm methanol and treated with 1M HCl in ether. After 2 hours at room temperature, the solvent was removed by rotary evaporation and the residue recrystallized from methanol/ether to give 4-(p-cyclohexylmethoxyanilino)-6-methylsulfonamido-2-phenylquinoline hydrochloride (38%) as a pale yellow solid.

Provenance & Evidence