Bromine → 5-Bromo-2-hydroxy-4-methyl-3-nitropyridine

HRID 1005402Notes

Reaction equation

HRID 1005402 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[N+:9]([O-:11])=[O:10].C([O-])(=O)C.[Na+].[Br:17]Br>C(O)(=O)C.C(OCC)(=O)C>[Br:17][C:7]1[C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[C:4](=[O:8])[NH:5][CH:6]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 3453702-Hydroxy-4-methyl-3-nitropyridineHCID 517045Sodium Acetate

Product 1

HCID 217065175-Bromo-2-hydroxy-4-methyl-3-nitropyridineYield 90%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-methyl-3-nitro-2-pyridone (0.45 g, 2.9 mmol) in glacial acetic acid (3 mL) was added sodium acetate (0.24 g) followed by bromine (0.15 mL) dropwise. After 5.5 hours, the mixture was diluted with ethyl acetate, washed with water, dried, filtered and concentrated to give 5-bromo-4-methyl-3-nitro-2-pyridone (0.62 g, 2.6 mmol, 90%).

Workup

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7220faf6d534434d8c42bdc355799762
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Reaction notes

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