Ethanol → 4-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

HRID 1720428Notes

Reaction equation

HRID 1720428 reaction equation
[OH-].[K+].C(O)C.[F:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:9][C:8]=1[NH:20]C(=O)OC>O>[F:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:9][C:8]=1[NH2:20]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 15766845methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate

Product 1

HCID 152793894-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamineYield 98.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 4N potassium hydroxide aqueous solution (4.75 liters) was added to an ethanol solution (3 liters) of methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate (2.25 Kg, 7.85 mol), followed by refluxing under heating for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, water (5 liters) was added thereto, and the mixture was extracted with toluene (5 liters×2 portions). The organic layer was washed with water and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and the filtrate was distilled off under reduced pressure to obtain 2-fluoro-4-chloro-5-cyclopentyloxyaniline as an oily substance (1.75 Kg, 7.62 mol, 98.3% yield).

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 5 hours
  3. customAfter completion of the reaction
  4. extractionthe mixture was extracted with toluene (5 liters×2 portions)
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe drying agent was separated by filtration
  8. distillationthe filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9303ea6f76ae414492fb0f6becff9ab9
Source dataset
uspto-grants-1996_04
Patent number
US05506190

Reaction notes

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