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

HRID 2370868Notes

Reaction equation

HRID 2370868 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:14])=[N+:11]([O-:13])[CH:12]=1.[OH-].[Na+]>CCOC(C)=O>[CH3:5][O:6][C:7]1[C:8]([N+:1]([O-:4])=[O:2])=[CH:9][C:10]([CH3:14])=[N+:11]([O-:13])[CH:12]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 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 8857Ethyl AcetateSolvent

Procedure

To fuming nitric acid (20 mL, Spectrochem, India) was added (5-methoxy-2-methylpyridine 1-oxide (14 g, 0.100 mol) in one lot and the reaction was stirred at rt for 2 h. Reaction progress was monitored by TLC (50% EtOAc in pet ether.). After completion of the reaction, the reaction mixture was poured in to ice water (100 mL) and neutralized with 40% NaOH solution (PH ˜7-7.5) to get a yellow precipitate. The precipitate was stirred for 5-10 min, then filtered and dried to give the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.51 (s, 1H), 8.21 (s, 1H), 3.95 (s, 3H), 2.31 (s, 3H). MS (ESI, positive ion) m/z: 184.8 (M+H).

Workup

  1. customReaction progress
  2. customAfter completion of the reaction
  3. customto get a yellow precipitate
  4. stirringThe precipitate was stirred for 5-10 min
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-ea0ec9f6da4c4ab8bb0d4cfc9c07687a
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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