Methanol → 2-Methoxy-5-methyl-3-nitropyridine

HRID 72645

Reaction equation

HRID 72645 reaction equation
[Na].Cl[C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]([CH3:12])=[CH:5][N:4]=1.[CH3:13][OH:14]>>[CH3:13][O:14][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]([CH3:12])=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 8183002-Chloro-5-methyl-3-nitropyridineHCID 5360545Sodium

Product 1

HCID 269676032-Methoxy-5-methyl-3-nitropyridineYield 92%

Procedure

To a solution of sodium (2.31 g, 0.1 mol) dissolved in methanol (100 mL) at room temperature, 2-chloro-5-methyl-3-nitro-pyridine (17.2 g, 0.1 map was added. The reaction mixture was refluxed for 4 h under N2 atmosphere. After evaporated to dryness, the residue was diluted with water (100 mL) and extracted (2×50 mL CH2Cl2). The combined extracts were washed with brine, dried on MgSO4, and filtered. The solvent was evaporated and the residue was crystallized from a mixture of water (300 mL) and ethanol (20 mL) to yield 2-methoxy-5-methyl-3-nitro-pyridine as a light orange solid (15.4 g, 92%). 1H-NMR (DMSO-d6): δ 2.31 (s, 3H, CH3), 3.98 (s, 3H, OCH3), 8.30 (d, 1H, J=2.0 Hz, Py-H), 8.35 (d, 1H, J=2.0 Hz, Py-H); 13C-NMR (DMSO-d6): δ 16.80, 54.86, 127.36, 133.7, 135.91, 152.03, 154.27; HR-MS (ESI+) m/z 169.0570 [M+H]+; C7H8N2O3 requires 168.0535.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h under N2 atmosphere
  2. customAfter evaporated to dryness
  3. additionthe residue was diluted with water (100 mL)
  4. extractionextracted (2×50 mL CH2Cl2)
  5. washThe combined extracts were washed with brine
  6. customdried on MgSO4
  7. filtrationfiltered
  8. customThe solvent was evaporated
  9. customthe residue was crystallized from a mixture of water (300 mL) and ethanol (20 mL)

Sources & evidence

ORD record
ord-0121e54ac111427d952940d87bc6da12
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Linked notes

Loading…