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

HRID 1817365Notes

Reaction equation

HRID 1817365 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

HCID 690618815-Bromo-2-(3-chloro-4-fluorobenzyl)-8-methoxy-2,3,4,6-tetrahydro-2,6-naphthyridine-1,7-dione

Product 1

HCID 546986315-Bromo-2-(3-chloro-4-fluorobenzyl)-8-hydroxy-2,3,4,6-tetrahydro-2,6-naphthyridine-1,7-dione

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

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.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved in methanol
  3. concentrationconcentrated under vacuum
  4. customtriturated with anhydrous diethyl ether
  5. customThe solid precipitated
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-143148df916040b987edd4a2016e497a
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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