Reaction #53802

Reaction equation

sodium bicarbonate

4-Nitrobenzaldehyde

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

Sodium triacetoxyborohydride

→

product

Yield 38.8%

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

Yield 38.8%

Solvents

methylene chloride

acetic acid

Conditions

Workup

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
   Otherthe organic layer was separated
5. 5
   Dryingdried over Na2SO4
6. 6
   OtherThe solvent was evaporated
7. 7
   Otherto give an orange solid
8. 8
   OtherRecrystallization from ethyl acetate

Procedure

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.

Source