2-(4-amino-2-ethoxyphenyl)isoindole-1,3-dione

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 9.2 g (0.03 mole) of 2-(2-ethoxy-4-nitrophenyl)-1H-isoindol-1,3(2H)-dione and 12.8 g (0.23 mole) of iron powder in 50 ml of water was heated at 100° C. During a two hour period 35.1 g (0.58 mole) of glacial acetic acid was added to the hot reaction mixture. After complete addition the mixture was heated at reflux for four hours. The reaction mixture was cooled then made basic by the addition of potassium carbonate. The basic mixture was extracted with 500 ml of methylene chloride. The extract was filtered, and the filtrate extracted with 300 ml of 2N hydrochloric acid. The acidic extract was made basic with cold concentrated ammonium hydroxide. The basic solution was extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated under the reduced pressure to produce 3.1 g of 3-ethoxy-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)aniline as a solid. After complete addition the mixture was heated at reflux for four hours The reaction mixture was cooled The basic mixture was extracted with 500 ml of methylene chloride The extract was filtered the filtrate extracted with 300 ml of 2N hydrochloric acid The acidic extract The basic solution was extracted with methylene chloride The extract was dried over anhydrous sodium sulfate filtered the filtrate evaporated under the reduced pressure