Acetyl bromide → HCID 86703139, compound

HRID 2204333Notes

Reaction equation

HRID 2204333 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+]([O-])=O)=[CH:5][C:6]([CH3:10])=[N+:7]([O-:9])[CH:8]=1.C([Br:17])(=O)C>C(O)(=O)C>[Br:17][C:4]1[C:3]([O:2][CH3:1])=[CH:8][N+:7]([O-:9])=[C:6]([CH3:10])[CH:5]=1

Participants

4

Reactant 2

HCID 10482Acetyl bromideHCID 151634575-Methoxy-2-methyl-4-nitropyridine 1-oxide

Product 1

HCID 86703139HCID 86703139, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

5-Methoxy-2-methyl-4-nitro-pyridine-1-oxide (Step AL5) (1.9 g, 10.3 mmol) and acetyl bromide (22.9 mL, 310 mmol) was added to acetic acid (40 mL) and the reaction was stirred at 80° C. for 1 h. The mixture was concentrated (1/3) and a solution of NaOH was added. The resulting mixture was extracted with EtOAc, washed with brine, dried (Na2SO4), filtered and concentrated. The product was crystallised (EtOAc/TBME). ESI-MS: tR=0.54 min, [M+H]+ 218.1/220.1 (LC-MS 1).

Workup

  1. concentrationThe mixture was concentrated (1/3)
  2. additiona solution of NaOH was added
  3. extractionThe resulting mixture was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was crystallised (EtOAc/TBME)

Sources & evidence

ORD record
ord-f96c31e4869147be9d38b9522a6a9647
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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