Thionyl Chloride → 6-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carbonyl chloride
Reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([C:17](O)=[O:18])=[N:12][CH:11]=[C:10]([O:20][CH3:21])[C:9]=3[C:8]2=[O:22])=[CH:4][CH:3]=1.S(Cl)([Cl:27])=O>>[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([C:17]([Cl:27])=[O:18])=[N:12][CH:11]=[C:10]([O:20][CH3:21])[C:9]=3[C:8]2=[O:22])=[CH:4][CH:3]=1Participants
3
Procedure
A solution of 6-(4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid (1.11 g, 3.36 mmol) in thionyl chloride (0.4 g, 3.36 mmol) was heated to 110° C. After 0.5 hours, the product mixture was concentrated under vacuum. The residue was suspended in toluene, evaporated, then suspended in chloroform and evaporated to give the title compound. The product was assayed by quenching in methanol solution to produce the methyl ester. ES MS M+1=345 (methyl ester forms after quench in methanol)