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

HRID 1732867Notes

Reaction equation

HRID 1732867 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 (250 ml) 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-d6f0326b3a484b5ba354b692b59f8e97
Source dataset
uspto-grants-1980_12
Patent number
US04239708

Reaction notes

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