4-Chloro-2-fluoro-5-isopropoxy-nitrobenzene → 4-Chloro-2-fluoro-5-isopropoxyphenylaniline

HRID 2295939Notes

Reaction equation

HRID 2295939 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N+:12]([O-])=O)=[C:4]([F:15])[CH:3]=1.[H][H]>C(O)C.[Pt](=O)=O>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([NH:12][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:4]([F:15])[CH:3]=1

Participants

5

Reactant 2

HCID 131089864-Chloro-2-fluoro-5-isopropoxy-nitrobenzeneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 537633874-Chloro-2-fluoro-5-isopropoxyphenylanilineYield 69.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A suspension of 4-chloro-2-fluoro-5-isopropoxynitrobenzene (13.5 g) and platinum dioxide (0.4 g) in ethanol (300 ml) was subjected to catalytic reduction with hydrogen at room temperature (ca. 20° C.) under atmospheric pressure, whereby a designed amount of hydrogen was absorbed. The resultant mixture was filtered to remove insoluble materials, and the filtrate was concentrated. The residue was subjected to purification by silica gel chromatography to give 5.6 g of 4-chloro-2-fluoro-5-isopropoxyphenylaniline. nD24.5 1.5360.

Workup

  1. custom(ca. 20° C.)
  2. customwas absorbed
  3. filtrationThe resultant mixture was filtered
  4. customto remove insoluble materials
  5. concentrationthe filtrate was concentrated
  6. customThe residue was subjected to purification by silica gel chromatography

Sources & evidence

ORD record
ord-b8453d9918ef48f89528530a37a63316
Source dataset
uspto-grants-1984_01
Patent number
US04427438

Reaction notes

Loading…