تفاعل #49761

معادلة التفاعل

hydrochloric acid

methyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate

2-methylcyclopentyl p-toluenesulfonate

potassium hydroxide

→

2-fluoro-4-chloro-5-(2-methylcyclopentyl)oxyaniline

المردود 40.0%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas charged into a 50 cc round-bottom flask
2. 2
   درجة الحرارةwhile heating on an oil bath at 80° to 100° C
3. 3
   أخرىAfter completion of the reaction
4. 4
   استخلاصthe mixture was extracted with ethyl acetate (20 ml×3)
5. 5
   غسيلwashed with a saturated aqueous solution of sodium chloride
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   أخرىThe drying agent was removed by filtration
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   أخرىto obtain a crude product (1.51 g)
10. 10
    أخرىThe product was purified by silica gel column chromatography (development solvent: hexane/ethyl acetate=17/3)

الإجراء التجريبي

A solution of methyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate (1.53 g, 6.98 mmol) synthesized by the process described in Reference Example 3, 2-methylcyclopentyl p-toluenesulfonate (1.78 g, 6.99 mmol) and N,N-dimethylformamide (15 ml) was charged into a 50 cc round-bottom flask, and then potassium hydroxide (400 mg, 7.15 mmol) in a powder form was added thereto, followed by stirring for 7 hours while heating on an oil bath at 80° to 100° C. After completion of the reaction, the reaction solution was cooled to room temperature, 2N hydrochloric acid (50 ml) was added thereto, and the mixture was extracted with ethyl acetate (20 ml×3). The organic layers were combined, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off under reduced pressure to obtain a crude product (1.51 g). The product was purified by silica gel column chromatography (development solvent: hexane/ethyl acetate=17/3) to obtain 2-fluoro-4-chloro-5-(2-methylcyclopentyl)oxyaniline as a colorless oily substance (666 mg, 2.73 mmol, 40% yield).

المصدر