Water → 4-Bromo-6-methylpyridin-2-ol

HRID 2263542Notes

Reaction equation

HRID 2263542 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-dimethyl-formamide. The reaction mixture is heated to 110° C. for 30 minutes—subsequently, the mixture is 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. temperatureis 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-66539b5e6009450c83f8242bcdc45001
Source dataset
uspto-grants-2010_12
Patent number
US07851634B2

Reaction notes

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