2-Chloro-5-nitropyridin-4-amine → 4-Amino-2-methoxy-5-nitropyridine

HRID 2391748Notes

Reaction equation

HRID 2391748 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][O-:13].[Na+]>CO>[CH3:12][O:13][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 109100582-Chloro-5-nitropyridin-4-amineHCID 10942334Sodium Methoxide

Product 1

HCID 147626984-Amino-2-methoxy-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 36.9 g of 2-chloro-5-nitropyridin-4-amine (example E6) in 500 ml methanol were added 250 ml of a freshly prepared solution of sodium methoxide in methanol (5.7 g sodium) and the reaction mixture was refluxed for 12 h. About 500 ml methanol were distilled off and 500 ml of water were added. The resulting precipitate was filtered, washed with ice water and dried under vacuum to the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 12 h
  2. distillationAbout 500 ml methanol were distilled off
  3. addition500 ml of water were added
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with ice water
  6. dry with materialdried under vacuum to the title compound

Sources & evidence

ORD record
ord-79427f17aa874a13bd8704cebbe0f9f4
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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