Hydrochloric Acid → N-Hydroxyphthalimide

HRID 1181668Notes

Reaction equation

HRID 1181668 reaction equation
Cl.[C:2]1(=[O:12])[NH:6][C:5](=[O:7])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]12.C(O)(=O)C1C(=CC=CC=1)C(O)=[O:17]>N1C=CC=CC=1>[OH:17][N:6]1[C:2](=[O:12])[C:3]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:4]2[C:5]1=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1017Phthalic Acid2×HCID 6809Phthalimide

Product 1

HCID 10665N-HydroxyphthalimideYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a flask was added 50 mL of 1N hydrochloric acid, and powdery phthalimide (2.9 g, 20 mmol) was slowly added thereto with stirring. Then, the mixture was stirred at 97° C. for 3 hours to obtain an aqueous solution containing phthalic acid. Phthalic acid was recovered by condensing and filtering the aqueous solution. Then, after hydroxylamine hydrochloride NH2OH.HCl (1.39 g 40 mmol) was dissolved in 100 mL of pyridine, the recovered phthalic acid was added thereto, and stirred at 97° C. for 4 hour to form N-hydroxyphthalimide (2.3 g yield 71%).

Workup

  1. additionwas slowly added
  2. stirringThen, the mixture was stirred at 97° C. for 3 hours
  3. customto obtain an aqueous solution
  4. customPhthalic acid was recovered by condensing
  5. filtrationfiltering the aqueous solution
  6. stirringstirred at 97° C. for 4 hour

Sources & evidence

ORD record
ord-e97d1a17636e4464a54e2a5c6fe71400
Source dataset
uspto-grants-2007_10
Patent number
US07285684B2

Reaction notes

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