Acetyl bromide → HCID 89649601, compound

HRID 2207592Notes

Reaction equation

HRID 2207592 reaction equation
[C:1]([Br:4])(=[O:3])[CH3:2].[CH3:5][C:6]1[C:11]([CH3:12])=[C:10]([N+]([O-])=[O:14])[CH:9]=[CH:8][N+:7]=1[O-:16].C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C>[C:1]([O-:3])(=[O:14])[CH3:2].[Br:4][C:10]1[CH:9]=[CH:8][N+:7]([OH:16])=[C:6]([CH3:5])[C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 10482Acetyl bromideHCID 11430Potassium CarbonateHCID 1482232,3-Dimethyl-4-nitropyridine-N-oxide

Product 1

HCID 89649601HCID 89649601, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of acetyl bromide (67.45 mL, 912.28 mmol) in acetic acid (140 mL) was added 2,3-dimethyl-4-nitro-1-oxido-pyridin-1-ium [TCl](15.34 g, 91.23 mmol) portionwise under nitrogen. The reaction was then warmed to 80° C. for 3 hours. The reaction was cooled and poured into a beaker of ice, and then basified with K2CO3 [caution]. The aqueous was then extracted with EtOAc (600 mL) and the organics were washed with brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo. This gave 4-bromo-1-hydroxy-2,3-dimethyl-pyridin-1-ium acetate (D5)(18.12 g, 65.677 mmol, 72% yield);

Workup

  1. temperatureThe reaction was cooled
  2. additionpoured into a beaker of ice
  3. extractionThe aqueous was then extracted with EtOAc (600 mL)
  4. washthe organics were washed with brine (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8dc7eeb5a58f444db2685bcd4a250dc0
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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