Reaction #52737

Reaction equation

3′-ethoxy-3-nitrobiphenyl-4-acetic acid

→

6-(3-ethoxyphenyl)-2-oxindole

Yield 91.0%

Solvents

acetic acid

Conditions

Workup

1. 1
   TemperatureThe mixture was refluxed for 2 hours
2. 2
   TemperatureThe reaction mixture was cooled
3. 3
   Concentrationconcentrated to dryness
4. 4
   workup.ADDITIONThe residue was treated repeatedly with ethyl acetate
5. 5
   Filtrationfiltered
6. 6
   Otherto remove insolubles
7. 7
   WashThe filtrate was washed twice with 1 N hydrochloric acid and brine
8. 8
   Dryingdried over anhydrous sodium sulfate
9. 9
   Concentrationconcentrated

Procedure

Iron chips (2.4 g) were added in one portion to 4.6 g of 3′-ethoxy-3-nitrobiphenyl-4-acetic acid in glacial acetic acid (40 ml). The mixture was refluxed for 2 hours. The reaction mixture was cooled and concentrated to dryness. The residue was treated repeatedly with ethyl acetate and filtered to remove insolubles. The filtrate was washed twice with 1 N hydrochloric acid and brine, dried over anhydrous sodium sulfate and concentrated to give 3.5 g (91%) of 6-(3-ethoxyphenyl)-2-oxindole as a light brown solid.

Source