Hydrazine hydrate (1:1) → 2-Hydrazinyl-3-methyl-5-nitropyridine
Reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.O.[NH2:13][NH2:14]>CCO>[NH:13]([C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1)[NH2:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 2-chloro-3-methyl-5-nitropyridine (35 g, 200 mmol) in EtOH (400 mL) was added hydrazine hydrate (30.0 g, 600 mmol) and the resulting reaction mixture was stirred at 60° C. for 1 hr. The reaction mixture was cooled down with an ice bath, the resulting precipitate was filtrated off, washed with cold H2O and Et2O and dried at 50° C. under reduced pressure to afford the title product (25.40 g, 113 mmol, 98%) as a yellow solid. tR: 0.43 min (LC-MS 2); ESI-MS: 169 [M+H]+; ESI-MS: 167 [M−H]− (LC-MS 2).
Workup
- customthe resulting reaction mixture
- temperatureThe reaction mixture was cooled down with an ice bath
- filtrationthe resulting precipitate was filtrated off
- washwashed with cold H2O and Et2O
- customdried at 50° C. under reduced pressure
Sources & evidence
- ORD record
- ord-75187f2ea84e446a828f2ec5051596ef
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975417B2
Reaction notes
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