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

HRID 1262632Notes

Reaction equation

HRID 1262632 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 mixture of 4-chloro-2-fluoro-5-isopropoxy-nitrobenzene (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-7c9fe5bd2f2b4ee6b08fa7d03cc17540
Source dataset
uspto-grants-1984_06
Patent number
US04452981

Reaction notes

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