Nitric Acid → 5-Methoxy-2-methyl-4-nitropyridine 1-oxide

HRID 2204334Notes

Reaction equation

HRID 2204334 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[N+:7]([O-:9])[CH:8]=1.[N+:11]([O-])([OH:13])=[O:12]>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[CH:5][C:6]([CH3:10])=[N+:7]([O-:9])[CH:8]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 122140195-Methoxy-2-methyl-1-oxo-1lambda~5~-pyridine

Product 1

HCID 151634575-Methoxy-2-methyl-4-nitropyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

5-Methoxy-2-methylpyridine-1-oxide [35392-66-6] (6 g, 43.1 mmol) and nitric acid (18.4 mL, 431 mmol, 1.48 g/mL) was added to acetic acid (50 mL) and the reaction was stirred at 90° C. for 6 h. The mixture was concentrated (1/4) and neutralized at 0° C. was addition of ammonium hydroxide. The mixture was extracted with EtOAc, washed with brine and water, dried (Na2SO4), filtered and concentrated. The product crystallised during concentration. ESI-MS: tR=0.50 min, [M+H]+ 185.1 (LC-MS 1).

Workup

  1. concentrationThe mixture was concentrated (1/4)
  2. customneutralized at 0° C.
  3. additionaddition of ammonium hydroxide
  4. extractionThe mixture was extracted with EtOAc
  5. washwashed with brine and water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product crystallised during concentration

Sources & evidence

ORD record
ord-73e4b10d1aea41c2924ee116aab426c9
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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