2-Chloro-3-nitropyridine → 2-Methoxy-3-nitropyridine

HRID 266917

Reaction equation

HRID 266917 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11][O-:12].[Na+]>CO>[CH3:11][O:12][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 2532192-Methoxy-3-nitropyridineYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-3-nitropyridine (25 g, 0.157 mol) was suspended in methanol (300 ml) and sodium methoxide (17 g, 0.315 mol) was added. The mixture was refluxed for 2 hr and part of the solvent removed under reduced pressure. The reaction mixture was diluted with water (1 litre) and the precipitate collected by filtration. The white solid obtained was washed with more water and dried under vacuum to give the title compound (18.2 g, 75%). 1H NMR (CDCl3): 8.42 (dd, J=5, 2 Hz, 1H); 8.28 (dd, J=8, 2 Hz, 1H); 7.06 (dd, J=8, 5 Hz, 1H); 4.13 (s, 3H)

Workup

  1. temperatureThe mixture was refluxed for 2 hr
  2. custompart of the solvent removed under reduced pressure
  3. additionThe reaction mixture was diluted with water (1 litre)
  4. filtrationthe precipitate collected by filtration
  5. customThe white solid obtained
  6. washwas washed with more water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-686066c2b0da44208fe1b4661a3551e5
Source dataset
uspto-grants-1997_07
Patent number
US05652363

Linked notes

Loading…