Nitric Acid → HCID 22019211, compound

HRID 6890Notes

Reaction equation

HRID 6890 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 1 l 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 1 l 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-082f5c4b45dc497e883bc6aabeb2e2b5
Source dataset
uspto-grants-2006_08
Patent number
US07084163B2

Reaction notes

Loading…