Reaction #89969

Reaction equation

2-(1-hydroxy-1-methyl-ethyl)-1H-indole-6-carbonitrile

nitrobenzene

aluminum chloride

4-methoxybenzoyl chloride

→

title compound

Yield 40.1%

8-Methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Yield 40.1%

Solvents

Water

Conditions

Workup

1. 1
   workup.STIRRINGby stirring at room temperature for 3 hr
2. 2
   Extractionwas then extracted with ethyl acetate
3. 3
   DryingThe organic layer was dried over sodium sulfate
4. 4
   OtherThe drying agent was removed by filtration
5. 5
   Otherthe residues obtained
6. 6
   Concentrationafter concentration under reduced pressure
7. 7
   Otherwere purified by silica gel column chromatography (hexane/ethyl acetate)

Procedure

(Method 3) To nitrobenzene (5 ml) and aluminum chloride (400 mg, 3 mmol), 4-methoxybenzoyl chloride (400 mg, 2.3 mmol) was added. After stirring for 30 min at room temperature, 2-(1-hydroxy-1-methyl-ethyl)-1H-indole-6-carbonitrile (Compound AA6, 200 mg, 1 mmol) was added followed by stirring at room temperature for 3 hr. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (127 mg, 40%).

Source