Reaction #52793

Reaction equation

6-(3-methoxyphenyl)-2-oxindole

3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid

→

3-{2-[6-(3-methoxyphenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}-propionic acid

Yield 82.1%

Solvents

ethanol

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated
2. 2
   OtherThe precipitate that formed
3. 3
   Filtrationwas collected by filtration
4. 4
   Washwashed with water and hexane

Procedure

A mixture of 103 mg 6-(3-methoxyphenyl)-2-oxindole, 95 mg 3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid and piperidine (3 drops) in ethanol (2 mL) was heated in sealed tube to 90° C. and held there overnight. The reaction mixture was concentrated and acidified with 6 N hydrochloric acid. The precipitate that formed was collected by filtration and washed with water and hexane to give 156 mg of 3-{2-[6-(3-methoxyphenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}-propionic acid as a brown solid (82%).

Source