Methanol → 2-Methoxy-5-nitropyridine

HRID 868346Notes

Reaction equation

HRID 868346 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][OH:12].[H-].[Na+].O>O1CCCC1>[CH3:11][O:12][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 795252-Methoxy-5-nitropyridineYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 10 g of 2-chloro-5-nitropyridine and 2 g of dry methanol in 40 ml of dry tetrahydrofuran, 2.8 g of sodium hydride (about 60%, in oil) is added under cooling in an ice-water bath. The mixture is stirred at room temperature for 1 hour, and 30 ml of water is added. The mixture is extracted with three 40-ml portions of ethyl acetate, and the combined extracts are dried over magnesium sulfate. The solvent is distilled off to give 8.0 g of crude 2-methoxy-5-nitropyridine.

Workup

  1. temperatureunder cooling in an ice-water bath
  2. extractionThe mixture is extracted with three 40-ml portions of ethyl acetate
  3. dry with materialthe combined extracts are dried over magnesium sulfate
  4. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-2aa1a7a1e1b642e58911a5c1d4f975a7
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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