Hydrochloric Acid → 2-Chloro-m-phenylenediamine

HRID 1076980Notes

Reaction equation

HRID 1076980 reaction equation
Cl.C(O)C.[Cl:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:7]=1[N+:15]([O-])=O.[OH-].[Na+]>O>[Cl:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 118141-Chloro-2,6-dinitrobenzeneHCID 14798Sodium Hydroxide

Product 1

HCID 124029782-Chloro-m-phenylenediamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1 ml. of concentrated hydrochloric acid in 5 ml. of 5% ethanol is slowly added to a refluxing mixture of 10.1 g. of 1-chloro-2,6-dinitrobenzene, electrolytically reduced iron and 20 ml. of 50% ethanol. The mixture is heated at reflux for 2 hours. The mixture is allowed to cool slightly and the pH is adjusted to 8 with sodium hydroxide solution. The iron products are removed by filtration. The solvent is removed from the filtrate to leave a solid which is dissolved in water and extracted with methylene chloride. Removal of the solvents leaves an oily solid which upon recrystallization of from Skellysolve B gives off-white crystals of 2-chloro-1,3-diaminobenzene having a melting point of 82°-83.5° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool slightly
  4. customThe iron products are removed by filtration
  5. customThe solvent is removed from the filtrate
  6. customto leave a solid which
  7. extractionextracted with methylene chloride
  8. customRemoval of the solvents
  9. customleaves an oily solid which
  10. customupon recrystallization of from Skellysolve B

Sources & evidence

ORD record
ord-3dd4b306d1c74576a7246dc6622e0123
Source dataset
uspto-grants-1976_05
Patent number
US03959289

Reaction notes

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