Ethanol → 4-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine
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
Procedure
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) and the mixture was heated under reflux for 5 hours. After reaction, the reaction liquid was cooled to room temperature, water (5 liters) was added thereto, and this was extracted with toluene (5 liters×2). The organic layer was washed with water 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 an oily product of 2-fluoro-4-chloro-5-cyclopentyloxyaniline (1.75 kg, 7.62 mol). Yield: 98.3%. Spectral data and other data of the product are those as shown in Example 21.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 5 hours
- customAfter reaction
- customthe reaction liquid
- extractionthis was extracted with toluene (5 liters×2)
- washThe organic layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe drying agent was taken out by filtration
- customthe solvent was removed by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-e9f0fd87981d43609c256e0e0c49a7a1
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05344953
Reaction notes
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