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

HRID 1198781Notes

Reaction equation

HRID 1198781 reaction equation
[OH-].[Na+].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 14798Sodium HydroxideHCID 15766845methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate

Product 1

HCID 152793894-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamineYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2N sodium hydroxide aqueous solution (3.5 ml) was added to an ethanol solution (1.5 ml) of methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate (1.507 g, 5.24 mmol), and the mixture was heated under reflux for 2 hours. After reaction, the reaction liquid was cooled to room temperature, water was added thereto, and this was extracted with ethyl acetate (20 ml ×2). The organic layer was washed with water and saturated brine and then dried over anhydrous magnesium sulfate. The drying agent was taken out by filtration, and the solvent was removed by distillation under reduced pressure, to obtain 2-fluoro-4-chloro-5-cyclopentyloxyaniline (1.20 g, 5.22 mmol). Yield: ~100 %.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter reaction
  4. customthe reaction liquid
  5. extractionthis was extracted with ethyl acetate (20 ml ×2)
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent was taken out by filtration
  9. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-af67dee3f146436d8186ae507ecef234
Source dataset
uspto-grants-1994_01
Patent number
US05281742

Reaction notes

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