Nitric Acid → 4-Nitro-2,3,5-trimethylpyridine, 1-oxide

HRID 578048Notes

Reaction equation

HRID 578048 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][N+:3]=1[O-:10].S(=O)(=O)(O)O.[N+:16]([O-])([OH:18])=[O:17].C(=O)([O-])O.[NH4+]>O>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:16]([O-:18])=[O:17])[C:5]([CH3:9])=[CH:4][N+:3]=1[O-:10]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14013Ammonium BicarbonateHCID 104869072,3,5-Trimethyl-1-oxidopyridin-1-ium

Product 1

HCID 112176114-Nitro-2,3,5-trimethylpyridine, 1-oxideYield 81.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

2,3,5-trimethylpyridine 1-oxide (1.38 kg, 10.1 mol) was charged into 98% sulfuric acid (4.93 kg, 49.3 mol). 97% nitric acid (1.44 kg) was added dropwise to the solution over 50 minutes, and the solution was then heated for 4 hours at 85° C. The reaction solution was charged into a mixture of ammonium hydrogencarbonate (10.6 kg) and water (9.0 L), and the resultant mixture was extracted with ethyl acetate (3.0 L×3). The resultant organic layer was concentrated and then dried overnight under vacuum to obtain 1.50 kg of the title compound.

Workup

  1. extractionthe resultant mixture was extracted with ethyl acetate (3.0 L×3)
  2. concentrationThe resultant organic layer was concentrated
  3. customdried overnight under vacuum

Sources & evidence

ORD record
ord-34b4069a17dd427885967b0bf43e0010
Source dataset
uspto-grants-2015_05
Patent number
US09040564B2

Reaction notes

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