Nitric Acid → 2,6-Lutidine, 4-nitro-, 1-oxide

HRID 2354058Notes

Reaction equation

HRID 2354058 reaction equation
[N+:1]1([O-:9])[C:2]([CH3:8])=[CH:3][CH:4]=[CH:5][C:6]=1[CH3:7].[N+:10]([O-])([OH:12])=[O:11].OS(O)(=O)=O>>[CH3:8][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[C:6]([CH3:7])[N+:1]=1[O-:9]

Participants

4

Reactant 3

HCID 944Nitric Acid2×HCID 1118Sulfuric Acid2×HCID 140832,6-Dimethylpyridine N-oxide

Product 1

HCID 209452,6-Lutidine, 4-nitro-, 1-oxide

Conditions

Temperature
80 °C

Procedure

Lutidine-N-oxide (19 g, 155 mmol) is cooled at 0° C. and a mixture of fuming HNO3 (100%, 37.5 mL) and conc. H2SO4 (95-97%, 52.5 mL), prepared by addition of H2SO4 to HNO3 at 0° C., is added slowly. The mixture is heated at 80° C. for 3 h. The cooled mixture is carefully poured into ice-water (500 mL). A white precipitate forms that is filtered. The precipitate is dissolved in CH2Cl2 (100 mL) and the filtrate is extracted with CH2Cl2 (4×75 mL). The organic extracts are combined with the dissolved precipitate and washed with sat. aq. NaCl (2×75 mL), dried (Na2SO4), filtered and evaporated to provide the title compound.

Workup

  1. additionis added slowly
  2. filtrationA white precipitate forms that is filtered
  3. dissolutionThe precipitate is dissolved in CH2Cl2 (100 mL)
  4. extractionthe filtrate is extracted with CH2Cl2 (4×75 mL)
  5. washwashed with sat. aq. NaCl (2×75 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ab452c8e0e634c79883338a9dd5c08ca
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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