1,1-Dimethylhydrazine monohydrochloride → 1,3-Dimethyl-5-nitro-1h-indazole
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11](=O)[CH3:12].Cl.[CH3:15][N:16](C)[NH2:17]>C(O)C>[CH3:15][N:16]1[C:2]2[C:3](=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=2)[C:11]([CH3:12])=[N:17]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-(2-chloro-5-nitrophenyl)ethanone (500 mg, 2.5 mmol) in anhydrous ethanol (15 mL) was added 1,1-dimethylhydrazine hydrochloride (3.38 g, 35.0 mmol) under nitrogen protection. The mixture was heated at reflux for 10 h and evaporated under reduced pressure to afford crude 307a (3.0 g), which was used in the next step without further purification. MS-ESI: [M+H]+ 192.2
Workup
- temperatureThe mixture was heated
- temperatureat reflux for 10 h
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-d6d238392bb4429aa51a53ffd6491e77
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238655B2
Reaction notes
Loading…