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

HRID 22492Notes

Reaction equation

HRID 22492 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-diaminobenzeneYield 43%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium dithionite (85%, 19.7 g, 96 mmol) in water (100 ml) was added to a suspension of N-(4-iodophenyl)-2-nitroaniline (8 g, 24 mmol) in ethanol (400 ml). The resulting mixture was heated under reflux for 45 min, cooled, treated with dilute aqueous ammonia (300 ml) and concentrated under reduced pressure. The resulting white slurry was treated with dilute aqueous ammonia (200 ml), filtered, the collected solid washed with water (100 ml) and dried to give N-(4-iodophenyl)-2-aminoaniline (3.1 g, 43%) as a white solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 45 min
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. additionThe resulting white slurry was treated with dilute aqueous ammonia (200 ml)
  6. filtrationfiltered
  7. washthe collected solid washed with water (100 ml)
  8. customdried

Sources & evidence

ORD record
ord-39a596f385694ece84cf949ef172b34e
Source dataset
uspto-grants-1995_06
Patent number
US05428168

Reaction notes

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