Hydrochloric Acid → N-Hydroxyphthalimide

HRID 1181670Notes

Reaction equation

HRID 1181670 reaction equation
C1([O:7][N:8]2[C:12](=[O:13])[C:11]3=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]3[C:9]2=[O:18])CCCCC1.[Na].C(O)(=O)C1C(=CC=CC=1)C(O)=O.Cl.C1(=O)OC(=O)C2=CC=CC=C12>[OH-].[Na+]>[OH:7][N:8]1[C:9](=[O:18])[C:10]2=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]2[C:12]1=[O:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1017Phthalic Acid3×HCID 6811Phthalic AnhydrideHCID 5360545SodiumHCID 10467039N-cyclohexyloxyphthalimide

Product 1

HCID 10665N-HydroxyphthalimideYield 81%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a flask was added 50 mL of 1N sodium hydroxide aqueous solution, and powdery N-cyclohexyloxyphthalimide (4.9 g, 20 mmol) was slowly added thereto with stirring. The mixture was stirred at 97° C. for 5 hours to obtain an aqueous solution containing sodium salt of phthalic acid. To the aqueous solution was added diluted hydrochloric acid to convert into phthalic acid, and phthalic acid was recovered by condensation and filtration. To a flask were added the phthalic acid, 50 mL of pyridine and 0.05 g of sulfuric acid and stirred at 95° C. for 4 hours to obtain a mixture containing phthalic anhydride. Hydroxylamine hydrochloride NH2OH.HCl (2.8 g, 40 mmol) was added to the mixture, stirred at 50° C. for 3 hours to form N-hydroxyphthalimide (2.6 g, yield 81%).

Workup

  1. additionwas slowly added
  2. stirringThe mixture was stirred at 97° C. for 5 hours
  3. customto obtain an aqueous solution
  4. filtrationwas recovered by condensation and filtration
  5. additionTo a flask were added the phthalic acid, 50 mL of pyridine and 0.05 g of sulfuric acid
  6. stirringstirred at 95° C. for 4 hours
  7. customto obtain a mixture
  8. stirringstirred at 50° C. for 3 hours

Sources & evidence

ORD record
ord-20667cdae19d45ff8cbb00fa10c9afe7
Source dataset
uspto-grants-2007_10
Patent number
US07285684B2

Reaction notes

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