Nitric Acid → 2,6-Dimethyl-4-nitropyridine

HRID 259522

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N+:3]=1[O-].[N+:10]([O-])([OH:12])=[O:11].S(=O)(=O)(O)O>>[CH3:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=[C:4]([CH3:8])[N:3]=1

Participants

Reactant 3

HCID 944Nitric Acid

HCID 1118Sulfuric Acid

HCID 140832,6-Dimethylpyridine N-oxide

Product 1

HCID 43278952,6-Dimethyl-4-nitropyridine

Procedure

The 4-nitro substituted starting material is prepared by contacting 2,6-dimethylpyridine N-oxide with nitric acid and sulfuric acid thereby forming the 2,6-dimethyl-4-nitropyridine. The N-oxide is reduced to the pyridine compound with phosphorous trichloride and then oxidized to the 4-nitropyridine 2,6-dicarboxylic acid with potassium permanganate.

Workup

customis prepared

Sources & evidence

ORD record: ord-c1e2f84e27b74439a7f91bfc0a9321e3
Source dataset: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04038398

Linked notes

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