1,4-Naphthoquinone → 2,5-Dichloro-1,4-benzenediamine

HRID 2249027Notes

Reaction equation

HRID 2249027 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([Cl:12])=[CH:5][C:3]=1[NH2:4].[OH-].[Na+].C1(=O)C2C(=CC=CC=2)C(=O)C=C1.O.NN>O>[Cl:1][C:2]1[CH:8]=[C:7]([NH2:9])[C:6]([Cl:12])=[CH:5][C:3]=1[NH2:4]

Participants

6

Reactant 4

HCID 85301,4-NaphthoquinoneHCID 14798Sodium HydroxideHCID 231082,5-Dichloro-4-nitroanilineHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 299492,5-Dichloro-1,4-benzenediamineYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A reaction vessel was charged with 200 g of water, 41.4 g of pulverized 2,5-dichloro-p-nitroaniline, 6 g of sodium hydroxide, 0.3 g of 1,4-naphthoquinone and 25 g of an 80% solution of hydrazine hydrate in water. The contents of the vessel were agitated at 85° to 95° C. for 9 hours to complete the reaction. The reaction product was filtered, washed with water and dried to give 34.0 of 2,5-dichloro-p-phenylenediamine.

Workup

  1. customthe reaction
  2. filtrationThe reaction product was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ebc2c527c961478baf9a08a3ab5a1f48
Source dataset
uspto-grants-1991_08
Patent number
US05041672

Reaction notes

Loading…