2,5-Dichloro-3-nitropyridine → 5-Chloro-2-methoxy-3-nitropyridine

HRID 573981Notes

Reaction equation

HRID 573981 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([Cl:14])=[CH:7][N:6]=1>CO.O>[Cl:14][C:8]1[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]([O:2][CH3:1])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 80633312,5-Dichloro-3-nitropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 263702185-Chloro-2-methoxy-3-nitropyridineYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of sodium methoxide (0.84 g, 16.6 mmol) in methanol (4 mL) was added dropwise to a solution of 2,5-dichloro-3-nitropyridine (1.00 g, 5.2 mmol) in methanol (10 mL) and the mixture was stirred and heated to reflux. After 7 hours, the mixture was cooled and diluted with water and the precipitate was filtered, washed with water and dried to give the title compound (0.95 g, 97%) as a white solid.

Workup

  1. temperatureheated to reflux
  2. temperaturethe mixture was cooled
  3. filtrationthe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-f58b2ad35bd54b06b41f1ff38d91e32c
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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