Water → 4-iodo-1H-indazol-3-amine
Reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[C:4]#[N:5].O.[NH2:12][NH2:13].O>C(O)CCC>[I:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]2[C:3]=1[C:4]([NH2:5])=[N:12][NH:13]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 107.5 °C
Procedure
A mixture of 2-fluoro-6-iodobenzonitrile (2 g, 8.1 mmol) and hydrazine hydrate (4 mL) in n-butanol (40 mL) was heated to 105-110° C. for 5 hours, cooled to room temperature, poured into water, and extracted twice with ethyl acetate. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated to provide 1.88 g of the desired product. Rf=0.25 (5% methanol/dichloromethane).
Workup
- temperaturecooled to room temperature
- extractionextracted twice with ethyl acetate
- washThe combined extracts were washed with water and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-135a5ed89ebe4756a6a27829342c43be
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642776B2
Reaction notes
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