6-Bromo-4-hydroxy-3-phenylquinolin-2(1H)-one → 6-Bromo-2-methoxy-3-phenylquinoline

HRID 627471Notes

Reaction equation

HRID 627471 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:5]2O.O([CH3:22])[Na]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:22])[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:5]2

Participants

4

Reactant 2

HCID 867160566-Bromo-4-hydroxy-3-phenylquinolin-2(1H)-one2×HCID 178418582HCID 178418582, compound

Product 1

HCID 867160626-Bromo-2-methoxy-3-phenylquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100-mL round-bottom flask was placed a mixture of 6-bromo-2-chloro-3-phenylquinoline (550 mg, 1.73 mmol, Intermediate 4, step b) and NaOCH3 (931 mg, 17.2 mmol) in methanol (50 mL). The resulting mixture was refluxed for 5 hours and concentrated under vacuum. The residue was purified by chromatography (silica gel column, 1:5 EtOAc/petroleum ether) to provide the title compound as a white solid.

Workup

  1. customIn a 100-mL round-bottom flask was placed
  2. temperatureThe resulting mixture was refluxed for 5 hours
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by chromatography (silica gel column, 1:5 EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-534b53654c2d428db2cc2d91cc7a0a86
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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