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

HRID 363324Notes

Reaction equation

HRID 363324 reaction equation
[Na].Cl[C:3]1[N:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=1.[CH3:13][OH:14]>>[CH3:13][O:14][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 2531236-Chloro-2-methyl-3-nitropyridineHCID 5360545Sodium

Product 1

HCID 2304756-Methoxy-2-methyl-3-nitropyridineYield 91%

Procedure

0.46 gm (20 mMol) sodium were dissolved in 15 mL anhydrous methanol. To this solution were added 2.3 gm 6-chloro-3-nitro-2-picoline in portions. The resulting mixture was stirred for 18 hours at room temperature and then 1 hour at reflux. The reaction mixture was poured into 100 mL of ice water with vigorous stirring. The suspension was filtered and the solid dried at 30° C. under reduced pressure for 18 hours to provide 2.04 gm (91%) of the desired compound as a tan solid.

Workup

  1. temperature1 hour at reflux
  2. filtrationThe suspension was filtered
  3. customthe solid dried at 30° C. under reduced pressure for 18 hours

Sources & evidence

ORD record
ord-d84530deda304e1d8eb72b185ae5d2cd
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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