2-Chloro-4-nitrobenzonitrile → 4-Amino-2-chlorobenzonitrile
Reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]>O.NN>[Cl:1][C:2]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A portion of 2-chloro-4-nitrobenzonitrile (5 g, 0.027 m) was heated with hydrazine monohydrate (110 ml) until the reaction began. Another portion of 2-chloro-4-nitrobenzonitrile (35 g, 0.192 m) was added in predetermined amounts. Once the evolution of nitrogen gas ceased, the reaction mixture was refluxed approximately thirty minutes, and then poured into stirred ice water. The precipitate was filtered and the solid was crystallized from water to yield 2-chloro-4-aminobenzonitrile (25 g, 78%, mp 117° C.).
Workup
- temperaturethe reaction mixture was refluxed approximately thirty minutes
- additionpoured
- filtrationThe precipitate was filtered
- customthe solid was crystallized from water
Sources & evidence
- ORD record
- ord-00dd216749eb4b8bb83edd99435101ce
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04424371
Reaction notes
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