Dimethylformamide → HCID 86731094, compound

Participants

Reaction Steps

A solution of ethyl 6-chloro-3-hydroxy-2-oxo-1,2-dihydroquinoline-4-carboxylate (470 mg, 1.76 mmol), prepared following procedure described for Intermediate 16, was stirred in DMF (2 mL) at rt. Cs2CO3 (1430 mg, 4.39 mmol) was added followed by iodomethane (0.220 mL, 3.51 mmol). The resulting mixture was stirred at rt for 72 h. CH2Cl2 was added. The mixture was washed with H2O, brine, dried over MgSO4, filtered and concentrated to give an off-white solid ethyl 6-chloro-3-methoxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carboxylate (527 mg, 1.78 mmol, 101% yield) as the major product. A small amount of the O-alkylated side product ethyl 6-chloro-2,3-dimethoxyquinoline-4-carboxylate was observed by LC-MS but not isolated (<5%). LC-MS (ESI) 295.9 (M+H), RT=1.97 min (Method B).

Provenance & Evidence