Phthalic Anhydride → N-Hydroxyphthalimide

HRID 429526

Reaction equation

HRID 429526 reaction equation
[C:1]1(=O)[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.S([O-])([O-])(=O)=O.[OH:17][NH3+:18].O[NH3+]>O>[OH:17][N:18]1[C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]2[C:1]1=[O:6]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 24846Hydroxylamine sulfate

Product 1

HCID 10665N-Hydroxyphthalimide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

0.15 g (1.0 mmol) of phthalic anhydride was mixed with 0.2 to 1 equivalent of hydroxylammonium sulfate (see Table 1) and, optionally after the addition of water (see Table 1), heated to 130° C. in a sealed ampoule. The reaction times were varied for the individual mixtures in accordance with Table 1. The cooled reaction mixture was dissolved in d6-DMSO and analyzed using 1H-NMR spectroscopy. The yields are given in each case in Table 1.

Workup

  1. customThe reaction times
  2. customThe cooled reaction mixture
  3. dissolutionwas dissolved in d6-DMSO

Sources & evidence

ORD record
ord-e3ee272c6b29480f9ca62db9970c86f7
Source dataset
uspto-grants-2001_11
Patent number
US06316639B1

Linked notes

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