Methanol → 6-Chloro-2-methoxy-3-nitropyridine

HRID 2264186Notes

Reaction equation

HRID 2264186 reaction equation
[CH3:1][OH:2].[H-].[Na+].Cl[C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([Cl:15])[N:7]=1.O>C1(C)C(C)=CC=CC=1>[Cl:15][C:8]1[N:7]=[C:6]([O:2][CH3:1])[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24758Sodium hydrideHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 107977036-Chloro-2-methoxy-3-nitropyridineYield 78.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent3×

Procedure

Methanol (3.3 g, 103 mmol) in xylene (100 mL) was added dropwise to a stirred suspension of sodium hydride (60% in mineral oil, 2.72 g, 113 mmol) in xylene (300 mL) at 0° C. under an argon atmosphere. After 20 minutes, 2,6-dichloro-3-nitropyridine (20.0 g, 103 mmol) in xylene (300 mL) was added dropwise then the reaction was warmed to ambient temperature and stirred overnight. Water (200 mL) was then added and the two phases were separated. The organic layer was washed with water and brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography (10:1 hexanes/ethyl acetate) to give the title compound (15.3 g, 78%) as a white solid.

Workup

  1. customthe two phases were separated
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography (10:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-0fd5e80784114ec1bb0f4856e546e54e
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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