Phthalic Anhydride → N-Hydroxyphthalimide

HRID 922294Notes

Reaction equation

HRID 922294 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].[C:6]1(=O)[O:11][C:9](=[O:10])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12>O>[OH:3][N:2]1[C:9](=[O:10])[C:8]2[C:7](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]1=[O:11]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 10665N-HydroxyphthalimideYield 55.34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a 250 mL RB flask fitted with magnetic stirrer was charged with hydroxylamine hydrochloride (5 g, 73 mmol) in water, then slowly added 50% of NaOH solution. To this stirred solution, added phthalic anhydride (11.26 g, 76 mmol), stirred at 90° C. for 40 min. Then cooled to RT, yellowish solid was removed by filtration. The filtrate was neutralized with 30% of H2SO4 and solid was precipitated. The solid was filtered off on Buchner flask and dried under line vacuum to obtain the title compound (6.5 g, Yield: 55.34%): 1H NMR (300 MHz, DMSO-d6): δ 10.80 (s, 1H), 7.84 (s, 4H).

Workup

  1. customTo a 250 mL RB flask fitted with magnetic stirrer
  2. temperatureThen cooled to RT
  3. customyellowish solid was removed by filtration
  4. customwas precipitated
  5. filtrationThe solid was filtered off on Buchner flask
  6. customdried under line vacuum

Sources & evidence

ORD record
ord-483020fc6a374861a3fb15bb6cbcaa76
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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