Acetyl bromide → 4-Bromo-2,3-dimethylpyridine 1-oxide

HRID 352791Notes

Reaction equation

HRID 352791 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][N+:3]=1[O-:12].C([Br:16])(=O)C.C(=O)([O-])[O-].[NH4+].[NH4+]>>[Br:16][C:6]1[CH:5]=[CH:4][N+:3]([O-:12])=[C:2]([CH3:1])[C:7]=1[CH3:8]

Participants

4

Reactant 3

HCID 10482Acetyl bromideHCID 1482232,3-Dimethyl-4-nitropyridine-N-oxideHCID 517111Ammonium Carbonate

Product 1

HCID 589974274-Bromo-2,3-dimethylpyridine 1-oxide

Conditions

Temperature
50 °C

Procedure

To 2,3-Dimethyl-4-nitropyridine N-oxide (3.00 g) which had been cooled to 0° C., added was acetyl bromide (18.0 ml), followed by stirring at 50° C. for 20 minutes and then at 75° C. for 15 minutes. The reaction mixture was charged in ice water and neutralized with an aqueous solution of ammonium carbonate. The neutralized solution was separated using methylene chloride. The organic layer was dried over anhydrous sodium sulfate and the filtrate was concentrated, whereby a crudely purified product of 4-bromo-2,3-dimethylpyridine N-oxide was obtained.

Workup

  1. additionadded
  2. waitat 75° C. for 15 minutes
  3. customThe neutralized solution was separated
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8c6fda6a51f14930bce16d968b15977c
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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