4-Chloro-2-nitro-1-phenoxybenzene → 5-Chloro-2-phenoxyaniline

HRID 1109986Notes

Reaction equation

HRID 1109986 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([N+:15]([O-])=O)[CH:3]=1>C1COCC1.[Ni]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([NH2:15])[CH:3]=1

Participants

4

Reactant 1

HCID 8911814-Chloro-2-nitro-1-phenoxybenzene

Product 1

HCID 667385-Chloro-2-phenoxyanilineYield 105.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound of Example 8 (76 g, 0.3 mol) was hydogenated with RaNi in THF (2.4 L). The product was distilled to yield a yellow liquid (69.5 g, 100%), which had a boiling point of 145°-150° C./1.5 mmHg. This material was employed in Example 10 without further purication.

Workup

  1. distillationThe product was distilled

Sources & evidence

ORD record
ord-35bbd76f074146b4b5f7674f2b00094a
Source dataset
uspto-grants-1994_06
Patent number
US05324722

Reaction notes

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