Hydrochloric Acid → 2-Chloro-m-phenylenediamine

HRID 1704266Notes

Reaction equation

HRID 1704266 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 two 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 two 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-c63f33cb969e49c3968718539116dde4
Source dataset
uspto-grants-1978_11
Patent number
US04126617

Reaction notes

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