Acetic Acid → 1H-Isoindole-1,3(2H)-dione, 2-[4-(phenylamino)phenyl]-
Reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[OH2:15].[C:16]([OH:19])(=O)[CH3:17]>>[C:4]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C:16](=[O:19])[C:17]4=[CH:5][CH:6]=[CH:1][CH:2]=[C:3]4[C:4]3=[O:15])=[CH:10][CH:9]=2)[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1Participants
Procedure
In a four-necked reactor equipped with a cooler and a thermometer, 80 g (0.42 mol) of trimellitic anhydride and 76.7 g (0.42 mol) of 4-aminodiphenylamine were dissolved in a liter of acetic acid under a nitrogen gas stream. This solution was allowed to react while heated to reflux for 10 hours in an oil bath. After completion of the reaction, the reaction liquid was poured into two liters of water, and a reaction product was precipitated. Thereafter, the reaction product as a precipitated solid was suction filtered. The filter cake was washed sequentially with water and methanol, and then was dried in a vacuum dryer. Thus, 138.5 g of a purified reaction product was obtained as a yellow-green solid (yield in Step 1: 92%). In this manner, an Intermediate F formed from an N-(4-phenylaminophenyl)-phthalimide compound having a carboxyl group at the 4-position, as represented by the following formula (7):
Workup
- customIn a four-necked reactor equipped with a cooler
- customto react
- temperaturewhile heated
- temperatureto reflux for 10 hours in an oil bath
- customAfter completion of the reaction
- customthe reaction liquid
- customa reaction product was precipitated
- filtrationfiltered
- washThe filter cake was washed sequentially with water and methanol
- customwas dried in a vacuum dryer
- customThus, 138.5 g of a purified reaction product
- customwas obtained as a yellow-green solid (yield in Step 1: 92%)
Sources & evidence
- ORD record
- ord-614adcdedc7c4026a0b6241831db380f
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883888B2
Reaction notes
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