تفاعل #75526

معادلة التفاعل

acetic acid

Sodium cyanoborohydride

5-aminophthalide

CH2O H2O

→

title compound

المردود 66.0%

5-Dimethylaminophthalide

المردود 66.0%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to 0° C.
2. 2
   workup.STIRRINGThe mixture was then stirred at room temperature for 1 hour
3. 3
   أخرىevaporated under low pressure until no acetonitrile
4. 4
   استخلاصThe resulting mixture was extracted with ethyl acetate (2×125 mL)
5. 5
   غسيلThe combined organic extracts were washed with saturated NaHCO3 solution (125 mL) and brine (125 mL)
6. 6
   تجفيفdried over Na2SO4
7. 7
   أخرىevaporated to dryness
8. 8
   أخرىto give a light brown solid, which
9. 9
   أخرىwas triturated with hot MeOH (10 mL)

الإجراء التجريبي

Sodium cyanoborohydride (8.42 g, 134 mmol) was added into a stirred suspension of 5-aminophthalide (5.0 g, 33.5 mmol) and 37% CH2O/H2O solution (24.9 mL, 335 mmol) in 120 mL of acetonitrile. The mixture was stirred at room temperature for 1 hour, cooled to 0° C. and 120 mL of 10% aqueous acetic acid solution was added. The mixture was then stirred at room temperature for 1 hour, evaporated under low pressure until no acetonitrile remained. The resulting mixture was extracted with ethyl acetate (2×125 mL). The combined organic extracts were washed with saturated NaHCO3 solution (125 mL) and brine (125 mL), dried over Na2SO4 and evaporated to dryness to give a light brown solid, which was triturated with hot MeOH (10 mL) to give the title compound (3.9 g, 66%) as an off-white solid.

المصدر