2-Chloro-5-nitropyridin-4-amine → 4-Amino-2-methoxy-5-nitropyridine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperaturethe reaction mixture was refluxed for 12 h
- distillationAbout 500 ml methanol were distilled off
- addition500 ml of water were added
- filtrationThe resulting precipitate was filtered
- washwashed with ice water
- 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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