1-Amino 2-nitro-4-(2,2-dichloro-1-methylethenyl) benzene → 1,2-Diamino-4-(2,2-dichloro-1-methylethenyl) benzene

HRID 46622Notes

Reaction equation

HRID 46622 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])=[C:9]([Cl:11])[Cl:10])=[CH:4][C:3]=1[N+:13]([O-])=O>[Fe].C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])=[C:9]([Cl:10])[Cl:11])=[CH:4][C:3]=1[NH2:13]

Participants

4

Reactant 1

HCID 213924321-Amino 2-nitro-4-(2,2-dichloro-1-methylethenyl) benzene

Product 1

HCID 545190211,2-Diamino-4-(2,2-dichloro-1-methylethenyl) benzene

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2.1 g. (8.5 mmoles) of 1-amino 2-nitro-4-(2,2-dichloro-1-methylethenyl) benzene 2.1 g. (0.038 moles) of iron powder is suspended in 80 ml. of 40% ethanol and refluxed for 30 minutes. The reaction mixture is filtered while hot, the solid material washed with ethanol and extracted with chloroform and evaporated to dryness in vacuo affording 1.66 g. of a brown glassy substance, which is used as is in the next step.

Workup

  1. additionA mixture of 2.1 g
  2. filtrationThe reaction mixture is filtered while hot, the solid material
  3. washwashed with ethanol
  4. extractionextracted with chloroform
  5. customevaporated to dryness in vacuo
  6. customaffording 1.66 g

Sources & evidence

ORD record
ord-a98c89a3bfa24d5f82668d0f52283d80
Source dataset
uspto-grants-1979_11
Patent number
US04174400

Reaction notes

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