2-Fluoro-4-chloro-5-cyclopentyloxynitrobenzene → 4-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

HRID 21475

Reaction equation

HRID 21475 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[N+:15]([O-])=O>C1(C)C=CC=CC=1.[C].[Pd]>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[NH2:15]

Participants

4

Reactant 1

HCID 193744702-Fluoro-4-chloro-5-cyclopentyloxynitrobenzene

Product 1

HCID 152793894-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 1140TolueneSolvent

Procedure

The resulting 2-fluoro-4-chloro-5-cyclopentyloxynitrobenzene (13.0 g, 50.1 mmol) was dissolved in toluene (100 ml), a catalytic amount of 10% palladium-carbon (0.5 g) was added thereto, and the mixture was reacted at room temperature to 70° C. under a hydrogen pressure of 3 to 5 atms. in a glass autoclave. After absorption of hydrogen gas ceased, the catalyst was removed by filtration, and the solvent was distilled off under reduced pressure from the filtrate to obtain substantially quantitatively oily 2-fluoro-4-chloro-5-cyclopentyloxyaniline. The spectral data and the like are as described in Reference Example 1.

Workup

  1. customthe mixture was reacted at room temperature to 70° C. under a hydrogen pressure of 3 to 5 atms
  2. customAfter absorption of hydrogen gas
  3. customthe catalyst was removed by filtration
  4. distillationthe solvent was distilled off under reduced pressure from the filtrate

Sources & evidence

ORD record
ord-67f78207c5b64f1ab0a8cb7a7aad0bee
Source dataset
uspto-grants-1995_06
Patent number
US05424277

Linked notes

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