Water → 4-Bromo-6-methylpyridin-2-ol

HRID 252357Notes

Reaction equation

HRID 252357 reaction equation
P(Br)(Br)([Br:3])=O.O[C:7]1[CH:12]=[C:11]([CH3:13])[NH:10][C:9](=[O:14])[CH:8]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Br:3][C:7]1[CH:12]=[C:11]([CH3:13])[NH:10][C:9](=[O:14])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24613Phosphorus oxybromideHCID 546914196-Methylpyridine-2,4-diol

Product 1

HCID 231494724-Bromo-6-methylpyridin-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

16 mmol of phosphorus oxybromide are added under an argon atmosphere to a solution of 21 mmol of 4-hydroxy-6-methyl-1H-pyridin-2-one [3749-51-7] in 9 ml of N,N-dimethylformamide. The reaction mixture is heated to 110° C. for 30 minutes and subsequently cooled to room temperature, and 10 ml of water are added. The solution is brought to pH 7 by adding sodium carbonate and cooled to 0° C. The precipitate is filtered off and washed with water and diethyl ether. The title compound is identified on the basis of the Rf value.

Workup

  1. temperaturesubsequently cooled to room temperature
  2. temperaturecooled to 0° C
  3. filtrationThe precipitate is filtered off
  4. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-4df7562c70004bd9a4222574ff17c932
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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