Phthalic Acid → N-Hydroxyphthalimide

HRID 1181669Notes

Reaction equation

HRID 1181669 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C(O)(=O)C1C(=CC=CC=1)C(O)=[O:16].C1(=O)OC(=O)C2=CC=CC=C12>Cl>[OH:16][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

5

Reactant 3

HCID 1017Phthalic AcidHCID 6809PhthalimideHCID 6811Phthalic Anhydride

Product 1

HCID 10665N-HydroxyphthalimideYield 70%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a flask was added 50 mL of 2N hydrochloric acid, and powdery phthalimide (7.4 g, 0.05 mol) 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, to a flask, were added the phthalic acid, 100 mL of pyridine and 0.5 g of sulfuric acid, and stirred for 3 hours at 100° C. with distilling off water formed by reaction to obtain a mixture containing phthalic anhydride. Hydroxylamine hydrochloride NH2OH.HCl (6.9 g, 0.1 mol) was added to the mixture and stirred at 50° C. for 3 hour to form N-hydroxyphthalimide (5.74 g, yield 70%).

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. additionThen, to a flask, were added the phthalic acid, 100 mL of pyridine and 0.5 g of sulfuric acid
  7. stirringstirred for 3 hours at 100° C.
  8. distillationwith distilling off water
  9. customformed by reaction
  10. customto obtain a mixture
  11. stirringstirred at 50° C. for 3 hour

Sources & evidence

ORD record
ord-ade979c8a64341a5bde95bf343a3652a
Source dataset
uspto-grants-2007_10
Patent number
US07285684B2

Reaction notes

Loading…