Phthalic Anhydride → Phthalimide, N-(m-hydroxyphenyl)-

HRID 1892072Notes

Reaction equation

[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[NH2:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1>CN(C)C=O>[OH:19][C:15]1[CH:14]=[C:13]([N:12]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])[CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 140 °C

Procedure

452 g (3.0 mol) of phthalic anhydride are used as initial charge in 1.6 l of DMF (dimethylformamide) in a round-bottomed flask. 334 g (3.0 mol) of 3-aminophenol are added slowly to this mixture. The mixture is stirred at 140° C. for 8 hours. During this period, water is removed by distillation by way of the head of a column. The mixture is permitted to cool to room temperature, and the precipitated solid is removed by suction filtration. The solid is washed first with water and then with ethanol, and is then dried in vacuo. This gives 650 g of a beige-coloured solid.

Workup

waitDuring this period
customwater is removed by distillation by way of the head of a column
temperatureto cool to room temperature
customthe precipitated solid is removed by suction filtration
washThe solid is washed first with water
dry with materialwith ethanol, and is then dried in vacuo

Sources & evidence

ORD record: ord-5891e349b13b498999120944d0ba2a0b
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507635B2

Reaction notes

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