Hydrochloric Acid → 4-Hydrazinyl-2-methylbenzonitrile hydrochloride
Reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.O.[NH2:12][NH2:13].O.[ClH:15]>C(O)C.C(OCC)C>[ClH:15].[NH:12]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1)[NH2:13]Participants
7
Conditions
- Temperature
- 80 °C
Procedure
In a dried reaction flask, 4-fluoro-2-methylbenzonitrile (4.055 g, 30.0 mmol) and hydrazine hydrate (85%) (3.54 mL, 60.0 mmol) were dissolved in ethanol (15.9 mL). In the protection from light and under the nitrogen atmosphere, the solution was heated under reflux at 80° C. for 48 hr. Water was added to the reaction solution. The mixture was filtered. The filtered cake was rinsed with water to produce a pale yellow solid, which was suspended in ethyl ether. A hydrogen chloride gas was passed into the suspension under an ice-salt bath. The suspension was filtered. The filtered cake was rinsed with ethyl ether to produce an off-white solid (2.04 g) in 37.0% yield.
Workup
- temperatureIn the protection from light and under the nitrogen atmosphere, the solution was heated
- filtrationThe mixture was filtered
- washThe filtered cake was rinsed with water
- customto produce a pale yellow solid, which
- filtrationThe suspension was filtered
- washThe filtered cake was rinsed with ethyl ether
Sources & evidence
- ORD record
- ord-7652479c111b45d9ae032b378636f5f2
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946279B2
Reaction notes
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