1-Chloro-2,4-Dinitrobenzene → 4-Chloro-M-phenylenediamine

HRID 1636636Notes

Reaction equation

HRID 1636636 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[N+:11]([O-])=O.[H][H]>[Ni].CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[NH2:11]

Participants

5

Reactant 2

HCID 61-Chloro-2,4-DinitrobenzeneHCID 178418361HCID 178418361, compound3×

Product 1

HCID 212094-Chloro-M-phenylenediamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of 1-chloro-2,4-dinitrobenzene (40.0 g, 0.197 mole), methanol (100 g), and 3.0 g of modified Raney nickel catalyst consisting of about 83.1% Ni, 9.3% Co, 7.1% Al and 0.5% Mo was charged into an autoclave. The autoclave was sealed, pressurized with hydrogen to 700 psig, and the hydrogenation carried out at about 30° C. Hydrogen uptake was observed by monitoring the pressure change. After the hydrogen uptake ceased (approximately 6.0 hrs.), the reaction mixture was heated for a short time longer and then the autoclave was vented. A sample of the reaction mixture was taken and analyzed by liquid chromatography after being separated from the solid catalyst. The desired product 1-chloro-2,4-diaminobenzene was formed in high yield and good purity. Liquid chromatography indicated an area % of 92.4% (excluding the methanol solvent) for the product. Very little dechlorination had occurred.

Workup

  1. additionwas charged into an autoclave
  2. customThe autoclave was sealed
  3. customcarried out at about 30° C
  4. custom(approximately 6.0 hrs.)
  5. temperaturethe reaction mixture was heated for a short time longer
  6. customafter being separated from the solid catalyst

Sources & evidence

ORD record
ord-35571003b8c145a28d57460cb076d554
Source dataset
uspto-grants-2000_03
Patent number
US06034276

Reaction notes

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