Sodium Nitrite → 7-methoxy-3-phenyl-1H-pyrazolo[3,4-c]pyridine
Reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH3:15])[C:9]=1[NH2:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:17]([O-])=O.[Na+]>C(O)(=O)C.O>[CH3:15][O:14][C:10]1[N:11]=[CH:12][CH:13]=[C:8]2[C:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:17][NH:16][C:9]=12Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-benzyl-2-methoxypyridin-3-amine (8.8 g) in acetic acid (310 mL) was added an aqueous solution prepared by dissolving sodium nitrite (2.83 g) in water (15.5 mL) at 0° C., and the mixture was stirred at 0° C. for 10 min, and then overnight at room temperature. The reaction mixture was concentrated under reduced pressure, to the residue was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethanol and hexane to give the title compound (5.2 g).
Workup
- customprepared
- customovernight
- customat room temperature
- concentrationThe reaction mixture was concentrated under reduced pressure, to the residue
- additionwas added saturated aqueous sodium hydrogencarbonate solution
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was crystallized from ethanol and hexane
Sources & evidence
- ORD record
- ord-1ede189198d1426f94d2c2af73cceec6
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09371320B2
Reaction notes
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