Isopropanol → 1,4-Benzenediamine, 2,5-dichloro-

HRID 2249026Notes

Reaction equation

HRID 2249026 reaction equation
C(O)(C)C.[Cl:5][C:6]1[CH:12]=[C:11]([N+:13]([O-])=O)[C:10]([Cl:16])=[CH:9][C:7]=1[NH2:8].[OH-].[Na+].O.NN>O.C1(=O)C2C(=CC=CC=2)C(=O)C=C1>[Cl:5][C:6]1[CH:12]=[C:11]([NH2:13])[C:10]([Cl:16])=[CH:9][C:7]=1[NH2:8]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 231082,5-Dichloro-4-nitroanilineHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 299491,4-Benzenediamine, 2,5-dichloro-Yield 91%

Reagents, catalysts & solvents 2

HCID 85301,4-NaphthoquinoneCatalystHCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

A reaction vessel was charged with 60 g of isopropyl alcohol, 50 g of water, 41.4 g of 2,5-dichloro-p-nitroaniline, 6 g of sodium hydroxide and 0.3 g of 1,4-naphthoquinone. The temperature of the mixture was controlled to be 75° to 80° C., and 22 g of an 80% solution of hydrazine hydrate in water was added dropwise to the mixture over 2 hours. After the addition, the reaction mixture was refluxed with stirring for 3 hours to complete the reaction. After cooling to 5° C., the reaction product was filtered, washed with water and dried, to give 32.2 g of 2,5-dichloro-p-phenylenediamine.

Workup

  1. customto be 75° to 80° C.
  2. additionAfter the addition
  3. temperaturethe reaction mixture was refluxed
  4. customthe reaction
  5. filtrationthe reaction product was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-0e4b2edc582e44ebb4b1a966d675a74b
Source dataset
uspto-grants-1991_08
Patent number
US05041672

Reaction notes

Loading…