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

HRID 1825496Notes

Reaction equation

HRID 1825496 reaction equation
[H-].[Na+].[CH3:3][OH:4].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:4][CH3:3])[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-nitropyridine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent3×

Procedure

To a suspension of sodium hydride (684 mg, 28.49 mmol) in xylene (100 ml), methanol (0.98 ml, 25.9 mmol) in xylene (30 ml) was added under nitrogen. The mixture was stirred for 20 min. A solution of 2,6-dichloro-3-nitropyridine (5.0g, 25.9mmo) in xylene (100 ml) was added to the reaction mixture and stirred at room temperature overnight. Water (50 ml) was added and the organic layer was separated. The organics was washed with water (1×50 ml) and brine (2×50 ml), dried, and concentrated in vacuo. The crude product was purified by flash chromatography (10:1 methylene chloride and acetone) to provide the desired compound, 6-chloro-2-methoxy-3-nitro-pyridine, as the only isomer as light yellow solid (90%).

Workup

  1. additionwas added under nitrogen
  2. stirringstirred at room temperature overnight
  3. customthe organic layer was separated
  4. washThe organics was washed with water (1×50 ml) and brine (2×50 ml)
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (10:1 methylene chloride and acetone)

Sources & evidence

ORD record
ord-5b628fde44e8442f8372669d5d697525
Source dataset
uspto-grants-2006_05
Patent number
US07045519B2

Reaction notes

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