Water → Methyl 5-bromo-6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 512470Notes

Reaction equation

HRID 512470 reaction equation
[F:1][CH:2]([F:14])[C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.[Br:15]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:15][C:4]1[CH:5]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[C:7](=[O:9])[NH:8][C:3]=1[CH:2]([F:1])[F:14]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 69233637HCID 69233637, compound

Product 1

HCID 69236839Methyl 5-bromo-6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.1 g (20 mmol) of methyl 6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate were dissolved in 20 ml of N,N-dimethylformamide, and 5.35 g (30 mmol) of N-bromosuccinimide were added at room temperature. After 2 hours of stirring, the reaction mixture was added to water and extracted with tert-butyl methyl ether. The extract was subsequently washed repeatedly with water. Drying and concentration finally gave 3.7 g (65% of theory) of the product.

Workup

  1. extractionextracted with tert-butyl methyl ether
  2. washThe extract was subsequently washed repeatedly with water
  3. customDrying
  4. concentrationconcentration finally gave 3.7 g (65% of theory) of the product

Sources & evidence

ORD record
ord-374f7bf6638446caa2ebc9c61dded4bc
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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