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

HRID 31721

Reaction equation

HRID 31721 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][N+:8]=1[O-:15].[N+:16]([O-])([OH:18])=[O:17].C(=O)([O-])O.[NH4+]>O>[CH3:6][C:7]1[C:12]([CH3:13])=[C:11]([N+:16]([O-:18])=[O:17])[C:10]([CH3:14])=[CH:9][N+:8]=1[O-:15]

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

To 98% sulfuric acid (4.93 kg, 49.3 mol), 2,3,5-trimethylpyridine1-oxide (1.38 kg, 10.1 mol) was added. After 97% nitric acid (1.44 kg) was added dropwise thereto over 50 minutes, the mixture was heated at 85° C. for 4 hours. The reaction mixture was poured to a mixture of ammonium hydrogen carbonate (10.6 kg) and water (9.0 L). The mixture was extracted with ethyl acetate (3.0 L×3). The obtained organic layer was concentrated and dried under vacuum overnight to obtain a desired product (1.50 kg).

Workup

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

Sources & evidence

ORD record
ord-96c5b1cc39524b49a713b86ca5077f65
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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