Bromine → 5-Bromo-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 1959310Notes

Reaction equation

HRID 1959310 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[C:10]#[N:11].[Br:12]Br>CC(O)=O>[Br:12][C:7]1[C:2]([CH3:1])=[C:3]([C:10]#[N:11])[C:4](=[O:9])[NH:5][C:6]=1[CH3:8]

Participants

4

Reactant 2

HCID 24408BromineHCID 698563-Cyano-4,6-dimethyl-2-hydroxypyridine

Product 1

HCID 7377525-Bromo-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrileYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred suspension of 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (5 g, 33.78 mmol) in AcOH (25 mL) was dropwise added bromine (2.5 mL) at rt. Resulting solution was stirred for 1 h. Solvent was removed under reduced pressure. Obtained solid was recrystallised in hot EtOH and H2O to give the title compound as a white solid (5.5 g, 72%).

Workup

  1. customat rt
  2. customSolvent was removed under reduced pressure
  3. customObtained solid
  4. customwas recrystallised in hot EtOH

Sources & evidence

ORD record
ord-a99087e896f440a0b03e6d46ba18f839
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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