Acetyl chloride → 4-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-ium

HRID 31614

Reaction equation

HRID 31614 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+]([O-])=O)[C:5]([CH3:12])=[CH:4][N+:3]=1[O-:13].C([Cl:17])(=O)C>>[Cl:17][C:6]1[C:5]([CH3:12])=[CH:4][N+:3]([O-:13])=[C:2]([CH3:1])[C:7]=1[CH3:8]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 112176114-Nitro-2,3,5-trimethylpyridine, 1-oxide

Product 1

HCID 27791414-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-ium

Procedure

The 2,3,5-trimethyl-4-nitropyridine1-oxide (13.4 g, 73.6 mmol) obtained in the step (11c) was added to acetyl chloride (80 ml, 1,125 mmol) at −30° C. in a nitrogen atmosphere. The mixture was stirred at −30° C. to room temperature for 4 hours and 20 minutes. After the reaction mixture was concentrated, the residue was subjected to silica gel column chromatography (NH silica gel: 300 g, elution solvent: heptane, heptane/ethyl acetate=50/50, ethyl acetate, ethyl acetate/methanol=10/1) to obtain fractions containing a pure product of the title compound and fractions containing a crude product of the title compound.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. washthe residue was subjected to silica gel column chromatography (NH silica gel: 300 g, elution solvent: heptane, heptane/ethyl acetate=50/50, ethyl acetate, ethyl acetate/methanol=10/1)
  3. customto obtain fractions

Sources & evidence

ORD record
ord-38466286cc2a4a64b9c890fc97eb9ba9
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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