تفاعل #53802

معادلة التفاعل

sodium bicarbonate

4-Nitrobenzaldehyde

5-(1H-indol-2-yl)-2-methoxy-phenylamine

Sodium triacetoxyborohydride

→

product

المردود 38.8%

[5-(1H-Indol-2-yl)-2-methoxy-phenyl]-(4-nitro-benzyl)-amine

المردود 38.8%

المذيبات

methylene chloride

acetic acid

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe resulting homogeneous solution was stirred at room temperature for 4 days
2. 2
   workup.STIRRINGthe mixture was stirred for 2 hours
3. 3
   workup.STIRRINGThe mixture was shaken
4. 4
   أخرىthe organic layer was separated
5. 5
   تجفيفdried over Na2SO4
6. 6
   أخرىThe solvent was evaporated
7. 7
   أخرىto give an orange solid
8. 8
   أخرىRecrystallization from ethyl acetate

الإجراء التجريبي

4-Nitrobenzaldehyde (0.302 g, 2.0 mmol) was added to a stirred mixture of 5-(1H-indol-2-yl)-2-methoxy-phenylamine (0.476 g, 2.0 mmol) in methylene chloride (125 mL), followed by acetic acid (0.2 g). The resulting mixture was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.46 g, 2.2 mmol) was added in one portion, and the resulting homogeneous solution was stirred at room temperature for 4 days. Saturated aqueous sodium bicarbonate solution (100 mL) was added and the mixture was stirred for 2 hours. The mixture was shaken, the organic layer was separated and dried over Na2SO4. The solvent was evaporated to give an orange solid. Recrystallization from ethyl acetate gave the product (290 mg), mp 198-199° C.

المصدر