HCID 13281436, compound → HCID 54117710, compound

HRID 1612965Notes

Reaction equation

HRID 1612965 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH3:11])=[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][CH2:9][CH2:10][CH3:11])=[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 13281436HCID 13281436, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54117710HCID 54117710, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A suspension of 4-chloro-2-fluoro-5-n-propoxynitrobenzene (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-n-propoxyphenylaniline. nD24.5 1.5386.

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-52e1a83705dc4b5298f52178d592674d
Source dataset
uspto-grants-1993_03
Patent number
US05191105

Reaction notes

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