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

HRID 1086675Notes

Reaction equation

HRID 1086675 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, compound

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 under room temperature and 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 obtain 5.6 g of 4-chloro-2-fluoro-5-isopropoxyphenylaniline. nD24.5 1.5360.

Workup

  1. customatmospheric pressure, whereby a designed amount of hydrogen was absorbed
  2. filtrationThe resultant mixture was filtered
  3. customto remove insoluble materials
  4. concentrationthe filtrate was concentrated
  5. customThe residue was subjected to purification by silica gel chromatography

Sources & evidence

ORD record
ord-447a48cdc5ed4201a4d2ddf66b44f942
Source dataset
uspto-grants-1991_07
Patent number
US05030761

Reaction notes

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