Sodium Hydroxide → 1-Phenyl-1H-pyrazol-4-amine
Reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)([O-])=O.[OH-].[Na+]>CCOC(C)=O>[C:9]1([N:7]2[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-nitro-1-phenyl-1H-pyrazole (440 mg, 2.32 mmol) and SnCl2 dihydrate (2.18 g, 9.66 mmol) in EtOAc (15 mL) was stirred at 80 C for 3 h. Aqueous 1N NaOH was added to bring pH to 12. The mixture was filtered through celite. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give 1-phenyl-1H-pyrazol-4-amine as a solid (173 mg).
Workup
- filtrationThe mixture was filtered through celite
- customThe organic phase was separated
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by HPLC
Sources & evidence
- ORD record
- ord-b2afcc78a4f849e5adf1b3cefc42b65e
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063058B2
Reaction notes
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