반응 #53802

반응 방정식

sodium bicarbonate

4-Nitrobenzaldehyde

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

Sodium triacetoxyborohydride

→

product

수율 38.8%

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

수율 38.8%

용매

methylene chloride

acetic acid

반응 조건

후처리

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
   기타the organic layer was separated
5. 5
   건조dried over Na2SO4
6. 6
   기타The solvent was evaporated
7. 7
   기타to give an orange solid
8. 8
   기타Recrystallization from ethyl acetate

실험 절차

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.

출처