Hydrochloric Acid → 5-amino-1-(2-fluoro-4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile
Reaction equation
C(O[C:4](=[C:6]([C:9]#[N:10])[C:7]#[N:8])[CH3:5])C.[F:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[NH:20][NH2:21].C(Cl)Cl.Cl>CCO>[NH2:10][C:9]1[N:20]([C:13]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=2[F:11])[N:21]=[C:4]([CH3:5])[C:6]=1[C:7]#[N:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 105 °C
Procedure
To a stirred solution of 2-(1-ethoxyethylidene)malononitrile (167 mg, 1.23 mmol) was added (2-fluoro-4-methoxyphenyl) hydrazine (220 mg, 1.41 mmol) in EtOH (3 mL). The solution was heated to 105° C. in the microwave for 30 min. CH2Cl2 and 1 M HCl was added and separated, the organic extract was washed with aqueous NaHCO3. The solution was dried using a phase separator and concentrated under reduced pressure to give 5-amino-1-(2-fluoro-4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (256 mg, 85%), which was used in the next step without further purification.
Workup
- customseparated
- extractionthe organic extract
- washwas washed with aqueous NaHCO3
- customThe solution was dried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8a99dcf7096b4a93ac32f0df757a3d88
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921402B2
Reaction notes
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