Tetrahydrofuran → 5-Chloro-3-iodobenzene-1,2-diamine

HRID 1417746Notes

Reaction equation

HRID 1417746 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:5]([NH2:6])=[C:4]([I:12])[CH:3]=1.O1CCCC1.[H][H]>C(O)CC>[Cl:1][C:2]1[CH:3]=[C:4]([I:12])[C:5]([NH2:6])=[C:7]([NH2:9])[CH:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 121435644-Chloro-2-iodo-6-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 540159985-Chloro-3-iodobenzene-1,2-diamineYield 96.3%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

1.5 g of 4-chloro-2-iodo-6-nitroaniline together with 50 ml of tetrahydrofuran and 10 ml of 1-propanol are initially introduced into a stirred autoclave. 5 mg of FeCl2.4H2O and 0.3 g Pt/Pb-CaCO3 catalyst are added to the solution, and hydrogenation is carried out at 130° C. and 20 bar of hydrogen. After the hydrogenation has come to a standstill, the reaction mixture is cooled to room temperature, the reactor is rendered inert with nitrogen and the catalyst is filtered off. After filtration, the solvent is removed by distillation to give 1.3 g of 4-chloro-6-iodo-1,2-phenylenediamine as a crude product.

Workup

  1. customis carried out at 130° C.
  2. filtrationthe catalyst is filtered off
  3. filtrationAfter filtration
  4. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-a96c476860a947fe84554ab6a145ed73
Source dataset
uspto-grants-1999_03
Patent number
US05877340

Reaction notes

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