5-Chloro-2-nitroaniline → 4-Chloro-1,2-diaminobenzene

HRID 375645

Reaction equation

HRID 375645 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([CH:8]=1)[NH2:7]>C(OCC)C.[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[C:6]([CH:8]=1)[NH2:7]

Participants

4

Reactant 1

HCID 742185-Chloro-2-nitroaniline

Product 1

HCID 72634-Chloro-1,2-diaminobenzene

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a suspension in diethyl ether (50 mL) of 5-chloro-2-nitroaniline (2.70 g, 15.6 mmol) was added zinc powder (10.2 g, 156 mmol) in portions. The reaction mixture was filtered and concentrated in vacuo to give 5-chloro-2-aminoaniline which as was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8942ec119ccc4365abfd9fb348b2641a
Source dataset
uspto-grants-1996_01
Patent number
US05486525

Linked notes

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