2-Ethylpropanedioyl dichloride → Ethyl 4-hydroxy-1-methyl-2-oxo-7-(trifluoromethyl)-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 2-(3-ethoxy-N-methyl-3-oxopropanamido)-6-(trifluoromethyl)nicotinate. A mixture of methyl 2-(methylamino)-6-(trifluoromethyl)nicotinate (0.300 g) and ethyl malonoyl chloride (0.19 mL, 1.6 mmol) in 1,2-dichloroethane (50 mL) was heated to 80° C. for 63 hours. The reaction mixture was allowed to reach room temperature and was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (gradient: 0-30% EtOAc/hexanes) to give the title compound. MS (ESI, pos. ion) m/z: 349 (M+1).

Provenance & Evidence