Ammonia → N-(4-iodophenyl)1,2-diaminobenzene

HRID 1460296Notes

Reaction equation

HRID 1460296 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[I:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-])=O)=[CH:12][CH:11]=1.N>O.C(O)C>[I:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH2:23])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24489Sodium DithioniteHCID 15045509N-(4-iodophenyl)-2-nitroaniline

Product 1

HCID 15045510N-(4-iodophenyl)1,2-diaminobenzene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

According to the method of Chem. Abs., 1962, 57, 9840a, a solution of sodium dithionite (85%, 24.74 g, 121 mmol) in water (120 ml) was added to a suspension of (4-iodophenyl)-2-nitroaniline in ethanol (500 ml). The mixture was heated under reflux for 45 minutes, cooled, treated with 300 ml of dilute aqueous ammonia, and concentrated under reduced pressure. The resulting white slurry was treated with 200 ml of dilute aqueous ammonia, filtered and washed with water (200 ml). The solid was dried in a vacuum desiccator at room temperature to give N-(4-iodophenyl)1,2-diaminobenzene, 8.91 g, which gradually darkens on exposure to light, m.p. 122°-123° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. additionThe resulting white slurry was treated with 200 ml of dilute aqueous ammonia
  6. filtrationfiltered
  7. washwashed with water (200 ml)
  8. customThe solid was dried in a vacuum desiccator at room temperature

Sources & evidence

ORD record
ord-3a7fbeb224eb463ab2e4e900593ba306
Source dataset
uspto-grants-1991_12
Patent number
US05070205

Reaction notes

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