Hydrochloric Acid → 5-Amino-1-methyl-1H-pyrazole-3-carbonitrile
Reaction equation
[CH3:1][N:2]1[C:6]([N+:7]([O-])=O)=[CH:5][C:4]([C:10]#[N:11])=[N:3]1.Cl>O.C(O)C.[Fe]>[NH2:7][C:6]1[N:2]([CH3:1])[N:3]=[C:4]([C:10]#[N:11])[CH:5]=1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
To a suspension of 1-methyl-5-nitro-1H-pyrazole-3-carbonitrile (2 g; 13.1 mmol) in a mixture of water (14 mL) and ethanol (120 mL) there are added HCl 37% (170 L) and iron filings (5.1 g; 91 mmol). The reaction mixture is heated for 5 hours at 50° C. After cooling to ambient temperature, the reaction mixture is filtered. The filtrate is concentrated to dryness and then purified by chromatography over silica gel using dichloromethane and ethyl acetate as eluants to yield the expected compound in the form of a solid.
Workup
- temperatureAfter cooling to ambient temperature
- filtrationthe reaction mixture is filtered
- concentrationThe filtrate is concentrated to dryness
- custompurified by chromatography over silica gel
Sources & evidence
- ORD record
- ord-5651e25f3e7c45f0840b557fb6762a2d
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108983B2
Reaction notes
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