Nitric Acid → HCID 22019211, compound

HRID 1442894Notes

Reaction equation

HRID 1442894 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[O:12][CH3:13].C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)O>[CH3:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([N+:1]([O-:4])=[O:2])[C:11]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 11430Potassium Carbonate2×HCID 47377664-Methoxy-3-methylpyridine

Product 1

HCID 22019211HCID 22019211, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

30 ml of 100% nitric acid is added to 150 ml of 98% sulphuric acid with stirring and cooling. To this solution is added dropwise 3.2 g (26 mmol) of 3-methyl-4-methoxy pyridine. The mixture is stirred at 80° C. for 2.5 hours, cooled down and added cautiously to a mixture of 400 g of crushed ice and 300 g of potassium carbonate with external cooling. 125 g more of potassium carbonate is added, and the suspension is filtered. The cake is washed with around 11 of diethyl ether. The filtrate layers are separated, the ethereal layer is dried, filtered off and concentrated to give 2.9 g (30% yield) of a yellow oil (M+1=169) (purity #80%, used with no further purification).

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at 80° C. for 2.5 hours
  3. temperaturecooled down
  4. filtrationthe suspension is filtered
  5. washThe cake is washed with around 11 of diethyl ether
  6. customThe filtrate layers are separated
  7. customthe ethereal layer is dried
  8. filtrationfiltered off
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0d80e3031c37456699b12033f46d0ee1
Source dataset
uspto-grants-2010_02
Patent number
US07659307B2

Reaction notes

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