Ammonia → 2-Amino-6-chloro-3-nitro-benzonitrile

HRID 1835091Notes

Reaction equation

HRID 1835091 reaction equation
Cl[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[C:3]=1[C:4]#[N:5].[NH3:14]>CCO>[NH2:14][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 44619322,6-Dichloro-3-nitrobenzonitrile

Product 1

HCID 112756272-Amino-6-chloro-3-nitro-benzonitrileYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A 500 mL pressure flask was charged with 2,6-dichloro-3-nitrobenzonitrile (30.0 g, 138 mmol) and a 5.1 M solution of ammonia in EtOH (170 mL). The flask was sealed and heated in an oil bath at 80° C. with stirring for 1.5 h. The cooled solution was filtered, the crystals washed with water and dried to yield 2-amino-6-chloro-3-nitrobenzonitrile (18.4 g, 68%), mp 181-184° C.; MS (ES−) 196, 198 (M−H−).

Workup

  1. customThe flask was sealed
  2. filtrationThe cooled solution was filtered
  3. washthe crystals washed with water
  4. customdried

Sources & evidence

ORD record
ord-47cec798682844fe9e433401071c5a20
Source dataset
uspto-grants-2004_08
Patent number
US06770639B2

Reaction notes

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