2-Chloro-4-nitrobenzonitrile → 4-Amino-2-chlorobenzonitrile

HRID 2295372

Reaction equation

HRID 2295372 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

HCID 1414012-Chloro-4-nitrobenzonitrile2×

Product 1

HCID 887284-Amino-2-chlorobenzonitrileYield 598.3%

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

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

  1. temperaturethe reaction mixture was refluxed approximately thirty minutes
  2. additionpoured
  3. filtrationThe precipitate was filtered
  4. customthe solid was crystallized from water

Sources & evidence

ORD record
ord-00dd216749eb4b8bb83edd99435101ce
Source dataset
uspto-grants-1984_01
Patent number
US04424371

Linked notes

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