Methanol → 4-(2,3-Dichloro-6-fluorophenyl)-1,4,5,6,7,8-hexahydro-2-methyl-7-phenyl-methyl-5-oxo-1,7-naphthyridine-3-carboxylic acid 2-(2,3-dichlorophenoxy)ethyl ester

Participants

Reaction Steps

Methanol (400 ml), 22.1 g (0.1 mole) of 1-benzyl-3-hydroxy-5-oxo-1,2,3,6-tetrahydropyridine hydrate, 19.3 g (0.1 mole) of 2,3-dichloro-6-fluorobenzaldehyde, 29.1 g (0.1 mole) of 2-(2,3-dichlorophenoxy)ethyl acetoacetate and 16 g (0.21 mole) of ammonium acetate were combined and heated to reflux. Solid began to precipitate after one-half hour, but refluxing was continued for 4 hours. The mixture was cooled to room temperature and filtered. The solid was washed with methanol, then dried in vacuo to obtain 34 grams (52.3%) of 4-(2,3-Dichloro-6-fluorophenyl)-1,4,5,6,7,8-hexahydro-2-methyl-7-phenyl-methyl-5-oxo-1,7-naphthyridine-3-carboxylic acid 2-(2,3-dichlorophenoxy)ethyl ester, m.p. 204°-6° C.

Provenance & Evidence