4-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)nitrobenzene → 4-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)aniline

HRID 704470

Reaction equation

HRID 704470 reaction equation
[H][H].[Cl:3][C:4]1[C:9]([O:10][CH2:11][C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:13])=[CH:8][C:7]([N+:20]([O-])=O)=[C:6]([F:23])[CH:5]=1>[C].[Pd].C1(C)C=CC=CC=1>[Cl:3][C:4]1[C:9]([O:10][CH2:11][C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:13])=[CH:8][C:7]([NH2:20])=[C:6]([F:23])[CH:5]=1

Participants

5

Reactant 2

HCID 146178494-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 146178504-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)anilineYield 62.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 1140TolueneSolvent

Procedure

Hydrogen gas (1.3 liters) was introduced into a mixture of the compound (III) (6.4 g), 5% palladium-carbon (0.32 g) and toluene (64 g) at room temperature while stirring in 1 hour. After removal of the catalyst from the reaction mixture, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give 4-chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)aniline (3.6 g). Yield, 62%.

Workup

  1. customAfter removal of the catalyst from the reaction mixture
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-40742a0820684252b4f6745369a24f59
Source dataset
uspto-grants-1991_01
Patent number
US04987247

Linked notes

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