Potassium Carbonate → 2-Bromo-4-methyl-3-nitro-pyridine

HRID 59958

Reaction equation

HRID 59958 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=O)[C:3]=1[N+:9]([O-:11])=[O:10].P(Br)(Br)([Br:14])=O.C(=O)([O-])[O-].[K+].[K+]>ClC(Cl)C>[Br:14][C:4]1[C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24613Phosphorus oxybromideHCID 3453702-Hydroxy-4-methyl-3-nitropyridine

Product 1

HCID 199260892-Bromo-4-methyl-3-nitro-pyridineYield 71.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

The 4-methyl-3-nitropyridin-2(1H)-one (110 g, 0.71 mol) was suspended in dichloroethane (1 L). The solution of phosphorus oxybromide (317 g, 1.1 mol) in dichloroethane (1 L) was added dropwise thereto at the ambient temperature. The reaction mixture was refluxed for 12 hours. The mixture was allowed to cool to room temperature, poured into ice water, and neutralized with potassium carbonate. The organic layer was separated, washed with water and brine, and dried over sodium sulfate. The solvent was evaporated to provide the title compound (yield 71.8%).

Workup

  1. customat the ambient temperature
  2. temperatureThe reaction mixture was refluxed for 12 hours
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ebac018909a54f20af991c206b66b15b
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Linked notes

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