Ammonium Chloride → 5-Chloro-1-ethyl-1H-pyrazol-4-amine
Reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[N:4]1)[CH3:2].[Cl-:11].[NH4+]>CCO.[Fe]>[Cl:11][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][C:6]=1[NH2:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a suspension of 1-ethyl-4-nitro-1H pyrazole (1 equiv) and iron dust (5 equiv) in EtOH (0.285 M) was added ammonium chloride (10 equiv). The mixture was heated to 80° C. for 20 h then cooled to room temperature. The solvent was removed under reduced pressure to give crude material that was purified by silica gel chromatography (1.5% MeOH in DCM) to provide the desired product (30% yield) as a yellow oil. MS (ESI) m/z 146.0 [M+H]+.
Workup
- temperaturethen cooled to room temperature
- customThe solvent was removed under reduced pressure
- customto give crude material that
- customwas purified by silica gel chromatography (1.5% MeOH in DCM)
Sources & evidence
- ORD record
- ord-81487a9393244daca69062cf8a628c38
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428509B2
Reaction notes
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