Hydrochloric Acid → N-Hydroxyphthalimide

HRID 1181667Notes

Reaction equation

HRID 1181667 reaction equation
[OH-].[Na+].[C:3]1(=[O:13])[NH:7][C:6](=[O:8])[C:5]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:4]12.[Na].C(O)(=O)C1C(=CC=CC=1)C(O)=[O:19].Cl>N1C=CC=CC=1>[OH:19][N:7]1[C:3](=[O:13])[C:4]2=[CH:12][CH:11]=[CH:10][CH:9]=[C:5]2[C:6]1=[O:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1017Phthalic Acid4×HCID 6809PhthalimideHCID 14798Sodium HydroxideHCID 5360545Sodium

Product 1

HCID 10665N-HydroxyphthalimideYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a flask was added 50 mL of 3N sodium hydroxide aqueous solution, and powdery phthalimide (8.8 g, 0.06 mol) was slowly added thereto with stirring. Then, the mixture was stirred at 97° C. for 2 hours to obtain an aqueous solution containing sodium salt of phthalic acid. To the aqueous solution was added diluted hydrochloric acid at ordinary temperature to convert into phthalic acid, and phthalic acid was recovered by condensation and filtration. Then, after hydroxylamine hydrochloride NH2OH.HCl (8.3 g, 0.12 mol) was dissolved in 100 mL of pyridine, the recovered phthalic acid was added thereto, stirred at 50° C. for 1 hour, and further stirred for 3 hours with elevating the temperature to 95° C. to form N-hydroxyphthalimide (7.3 g, yield 75%).

Workup

  1. additionwas slowly added
  2. stirringThen, the mixture was stirred at 97° C. for 2 hours
  3. customto obtain an aqueous solution
  4. filtrationwas recovered by condensation and filtration
  5. stirringstirred at 50° C. for 1 hour
  6. stirringfurther stirred for 3 hours
  7. customto 95° C.

Sources & evidence

ORD record
ord-09d967717bf443f7b6b3e5016da9cb8d
Source dataset
uspto-grants-2007_10
Patent number
US07285684B2

Reaction notes

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