Sodium Hydroxide → 2-iodo-1,4-benzenediamine

HRID 2164036Notes

Reaction equation

HRID 2164036 reaction equation
[I:1][C:2]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:3]=1[NH2:4].[OH-].[Na+]>Cl>[I:1][C:2]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2226292-Iodo-4-nitroaniline

Product 1

HCID 8191282-iodo-1,4-benzenediamineYield 20.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

A mixture of concentrated hydrochloric acid (150 ml) and 2-iodo-4-nitroaniline (30.0 g) is stirred and warmed to 45°-50° C. A solution of stannous chloride dihydrate (90.0 g) in concentrated hydrochloric acid (110 ml) is added while maintaining the reaction temperature at 65°-70° C. After the addition is completed, the mixture is cooled in an ice bath and 50% sodium hydroxide (250ml) is added slowly. The mixture is filtered and the isolated damp solid is stirred in 600 ml water at reflux. The solution is decolorized with charcoal, filtered and cooled to afford 5.55 g of title compound, m.p. 95°-99° C.

Workup

  1. temperaturewarmed to 45°-50° C
  2. temperaturewhile maintaining the reaction temperature at 65°-70° C
  3. additionAfter the addition
  4. temperaturethe mixture is cooled in an ice bath
  5. filtrationThe mixture is filtered
  6. stirringthe isolated damp solid is stirred in 600 ml water
  7. temperatureat reflux
  8. filtrationfiltered
  9. temperaturecooled

Sources & evidence

ORD record
ord-e89b797bacd648ef8d320c6a28a54741
Source dataset
uspto-grants-1979_01
Patent number
US04137310

Reaction notes

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