Ammonium Chloride → HCID 58926755, compound

Participants

Reaction Conditions

Reaction Steps

Mix 7-methyl-4-oxo-4H-[1,8]naphthyridine-1,3-dicarboxylic acid 3-ethyl ester 1-isopropyl ester (1.21 g, 3.80 mmol) and copper(I) iodide (1.59 g, 8.36 mmol) in THF (75 ml). Cool the mixture to −78° C. Inject ethyl magnesium bromide (3.0 M in diethyl ether, 7.60 ml) and stir for 2 h. Warm up to −20° C. and keep the reaction at that temperature for 3 h. Pour the reaction mixture into saturated ammonium chloride solution (100 ml). Extract with ethyl acetate (3×100 ml). Combine the organic layers, dry over sodium sulfate, filter and concentrate. Purify using silica gel column chromatography (gradient eluent, 0-60% ethyl acetate in hexane) to provide 2-ethyl-7-methyl-4-oxo-3,4-dihydro-2H-[1,8]naphthyridine-1,3-dicarboxylic acid 3-ethyl ester 1-isopropyl ester (0.715 g, 54%). MS (ES+): 349 (M+H).

Provenance & Evidence