Sodium Carbonate → HCID 178422452, compound

HRID 1924950Notes

Reaction equation

HRID 1924950 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4](O)[CH:3]=1.P(Br)(Br)([Br:12])=O.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O>[Br:12][C:4]1[CH:3]=[C:2]([CH3:1])[N:7]=[C:6]([OH:8])[CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24613Phosphorus oxybromideHCID 178429093HCID 178429093, compound

Product 1

HCID 178422452HCID 178422452, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 6-methylpyridine-2,4-diol (1.75 g, 14.0 mmol) in dry DMF (6.0 mL) is stirred under N2 and phosphorus oxybromide (3.05 g, 10.6 mmol) is added in one portion. The mixture is heated at 110° C. for 45 min and then cooled and diluted with water (7 mL). Na2CO3 (s) is added to bring the pH to 7 and the resulting suspension is cooled to 0° C. The product is collected by suction filtration, rinsing with cold water and diethyl ether, and dried overnight in a vacuum desiccator to afford the title compound as a light brown solid (920 mg).

Workup

  1. temperaturecooled
  2. temperaturethe resulting suspension is cooled to 0° C
  3. filtrationThe product is collected by suction filtration
  4. washrinsing with cold water and diethyl ether
  5. customdried overnight in a vacuum desiccator

Sources & evidence

ORD record
ord-97f5a04ce55a4c4b89eeafb4f8161c54
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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