Hydrazine → 6-Nitro-1H-indazol-3-amine
Reaction equation
F[C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:13][NH2:14]>C(O)(C)C>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][C:8]([N+:10]([O-:12])=[O:11])=[CH:7][CH:6]=2)[NH:14][N:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-fluoro-4-nitrobenzonitrile (10 mmol) in isopropanol (30 mL) was added aqueous hydrazine (4 mL). The resulting solution was heated at 80° C. for 12 h. The reaction mixture was then concentrated, water (30 mL) was added, and the solution was extracted with ethyl acetate (2×25 mL). The combined organics were washed with water (30 mL) and brine (30 mL) and dried over anhydrous sodium sulfate. The volatiles were removed in vacuo yielding 3-amino-6-nitroindazole as an orange solid, which was utilized for further transformation without further purification.
Workup
- concentrationThe reaction mixture was then concentrated
- additionwater (30 mL) was added
- extractionthe solution was extracted with ethyl acetate (2×25 mL)
- washThe combined organics were washed with water (30 mL) and brine (30 mL)
- dry with materialdried over anhydrous sodium sulfate
- customThe volatiles were removed in vacuo
Sources & evidence
- ORD record
- ord-8c9e1f7545c14c3a98e9efacf8bfd7a7
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377983B2
Reaction notes
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