Hydrazine → HCID 57636446, compound
Reaction equation
F[C:2]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH:7]([CH3:9])[CH3:8])=O.S(Cl)(Cl)=O.[NH2:21][NH2:22].C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[CH:7]([NH:6][C:4]1[C:3]2[C:2](=[CH:13][C:12]([N+:14]([O-:16])=[O:15])=[CH:11][CH:10]=2)[NH:22][N:21]=1)([CH3:9])[CH3:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
2-Fluoro-N-isopropyl-4-nitro-benzamide (0.204 g, 0.902 mmol) and thionyl chloride (1 mL) were heated to 78° C. and stirred for three hours. The reaction mixture was cooled and concentrated to a white solid. NMP (1 mL), hydrazine (0.28 mL, 8.92 mmol) and powdered K2CO3 were added, and the reation mixture was heated to 90° C. and stirred for two hours. The reaction mixture was cooled and partitioned between water and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed through silica gel (EtOAc/hexanes 0-33%) to give 0.075 g of Isopropyl-(6-nitro-1H-indazol-3-yl)-amine, MS (M+H)=249.
Workup
- temperatureThe reaction mixture was cooled
- concentrationconcentrated to a white solid
- stirringstirred for two hours
- temperatureThe reaction mixture was cooled
- custompartitioned between water and ethyl acetate
- customThe organic layer was separated
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was chromatographed through silica gel (EtOAc/hexanes 0-33%)
Sources & evidence
- ORD record
- ord-6f5ceb07b27a48f9b48d7511070db936
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07517901B2
Reaction notes
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