1,2-Dichloro-4-nitrobenzene → 3,4-dichloro-N-(propan-2-yl)aniline

HRID 486967Notes

Reaction equation

HRID 486967 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C(O[CH2:16][CH2:17][CH2:18]C)(=O)C>[Pt]>[CH:17]([NH:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)([CH3:18])[CH3:16]

Participants

4

Reactant 2

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 31272Butyl Acetate

Product 1

HCID 138030173,4-dichloro-N-(propan-2-yl)anilineYield 84.5%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

480.0 g (2.5 mol) of 3,4-dichloronitrobenzene were reacted in 2500 ml of butyl acetate under the reaction conditions described in Example 1 with 10 g of sulfited platinum catalyst F1OP. After the solvent had been distilled off in vacuo, the residue was fractionated to give 431.0 g of N-isopropyl-3,4-dichloroaniline at a purity of 98.9% (GC) in the boiling range 143° to 148° C. (13.33 to 16 bar), which corresponds to a yield of 84.5% of theory.

Workup

  1. distillationAfter the solvent had been distilled off in vacuo

Sources & evidence

ORD record
ord-e8e065b02ab740ee9aba937af52c2188
Source dataset
uspto-grants-1994_03
Patent number
US05292957

Reaction notes

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