Water → 4-Bromo-5-methoxyquinoline

HRID 1437362Notes

Reaction equation

HRID 1437362 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=O)[CH:6]=[CH:7][NH:8]2.P(Br)(Br)[Br:15].O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:15][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[CH:12][C:3]=2[O:2][CH3:1])[N:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 235953245-Methoxyquinolin-4-ol

Product 1

HCID 534078994-Bromo-5-methoxyquinolineYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of quinolone (c) (3.2 g, 18 mmol) in DMF (22 ml) was treated with phosphorous tribromide (2.2 ml). After 2 hours the mixture was added to water and neutralised with saturated aqueous sodium bicarbonate solution. Filtration and drying afforded a yellow solid (3.6 g, 85%).

Workup

  1. filtrationFiltration
  2. customdrying

Sources & evidence

ORD record
ord-89be9971a06b456681e9222a6f13db82
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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