Sulfuric Acid → N-Hydroxyphthalimide

HRID 1197918Notes

Reaction equation

HRID 1197918 reaction equation
[OH-:1].[Na+].Cl.[NH2:4]O.[C:6]1(=O)[O:11][C:9](=[O:10])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.S(=O)(=O)(O)O>O>[OH:1][N:4]1[C:9](=[O:10])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]2[C:6]1=[O:11]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6811Phthalic AnhydrideHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 10665N-HydroxyphthalimideYield 80.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of 42 g (1.05 mole) of sodium hydroxide in 500 ml of water, there was added 73.0 g (1.05 mole) of hydroxylamine hydrochloride. Subsequently, 148 g (1.0 mole) of phthalic anhydride was added to the solution and the resulting mixture was stirred at 90° C. for one hour. A solution of 30 g of sulfuric acid in 100 ml of water was added to the reaction mixture from which pale yellow solids had been precipitated out and the mixture was stirred for additional 30 minutes. The pale yellow solids were filtered off and recrystallized from a benzene/ethanol mixed solvent to give 132 g of the title compound: N-hydroxyphthalimide.

Workup

  1. customhad been precipitated out
  2. stirringthe mixture was stirred for additional 30 minutes
  3. filtrationThe pale yellow solids were filtered off
  4. customrecrystallized from a benzene/ethanol mixed solvent

Sources & evidence

ORD record
ord-3d77a75534784514ae078b438156c0f2
Source dataset
uspto-grants-1994_01
Patent number
US05278273

Reaction notes

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