Ammonia → HCID 22716668, compound

Participants

Reaction Steps

To a THF solution of 4-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]butanoic acid were added oxalyl chloride and one drop of DMF, followed by stirring at room temperature. The reaction mixture was added dropwise to an ice-cooled THF solution of concentrated aqueous ammonia and then, the whole was stirred for 30 minutes. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain 4-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]butanamide. To a dichloroethane solution of the resulting compound were added pyridine, phosphorus oxychloride and one drop of DMF, followed by stirring at room temperature. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain 4-(3-chlorophenyl)-3-(3-cyanopropyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one. NMR1: 6.90 (1H, d, J=8.2 Hz), 4.67 (2H, q, J=7.1 Hz), 1.70-2.10 (2H, m).

Provenance & Evidence