5-Bromo-2-(3-chloro-4-fluorobenzyl)-8-methoxy-2,3,4,6-tetrahydro-2,6-naphthyridine-1,7-dione → 5-Bromo-2-(3-chloro-4-fluorobenzyl)-8-hydroxy-2,3,4,6-tetrahydro-2,6-naphthyridine-1,7-dione
Reaction equation
[Br:1][C:2]1[NH:11][C:10](=[O:12])[C:9]([O:13]C)=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=1)[C:7]2=[O:15]>Br.C(O)(=O)C>[Br:1][C:2]1[NH:11][C:10](=[O:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=1)[C:7]2=[O:15]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5-bromo-2-(3-chloro-4-fluorobenzyl)-8-methoxy-2,3,4,6-tetrahydro-2,6-naphthyridine-1,7-dione (1.40 g, 3.37 mmol) in 33% HBr in acetic acid (20 mL) was stirred at room temperature for 1 hour. The product mixture was concentrated under vacuum. The residue was dissolved in methanol, concentrated under vacuum, and triturated with anhydrous diethyl ether. The solid precipitated was filtered to provide the titled compound.