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

HRID 704091

Reaction equation

HRID 704091 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).

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-656a2b2c6c0e4954967fca7975248aa6
Source dataset
uspto-grants-1991_01
Patent number
US04985570

Linked notes

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