Methanol → 6-Methoxy-2-methyl-3-nitropyridine

HRID 277987Notes

Reaction equation

HRID 277987 reaction equation
[Na].Cl[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([CH3:12])[N:4]=1.[CH3:13][OH:14]>>[CH3:13][O:14][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([CH3:12])[N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 2531236-Chloro-2-methyl-3-nitropyridineHCID 5360545Sodium2×

Product 1

HCID 2304756-Methoxy-2-methyl-3-nitropyridine

Conditions

Temperature
0 °C

Procedure

Sodium metal (8.68 g, 378 mmol) was added to methanol (350 mL) pre-cooled to 0° C. After the sodium completely dissolved, 2-chloro-5-nitro-6-methylpyridine (40.78 g, 236 mmol) was slowly added as a solid. The reaction mixture was heated at reflux temperature overnight, then poured into ice-water. The product was filtered and dried in vacuo overnight to give 29.39 grams of the title compound. (73%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature overnight
  3. filtrationThe product was filtered
  4. customdried in vacuo overnight

Sources & evidence

ORD record
ord-cd9a7fe90d97450d975dbaaf6ae09dc6
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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