Phthalic Acid → N-Anilinophthalimide

HRID 1638969Notes

Reaction equation

HRID 1638969 reaction equation
[C:1]([OH:12])(=O)[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([OH:6])=O.[C:13]1([NH:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Cl-].[Zn+2].[Cl-].O1CCOCC1>[C:13]1([NH:19][N:20]2[C:1](=[O:12])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 1017Phthalic AcidHCID 7516Phenylhydrazine

Product 1

HCID 101246N-AnilinophthalimideYield 30%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Phthalic acid (1.66 gram, 0.01 mole), phenylhydrazine (1.08 gram, 0.01 mole), and zinc chloride (3.0 gram, 0.022 mole) were added into 50 ml. of dioxane. After refluxing for 2 hours, the mixture was cooled to room temperature. The solvent was then removed and the residue was poured into ice-water which precipitated a yellow solid. After recrystallization from methanol, the pure compound was obtained in 30% yield as yellow needles (0.7 grams; m.p. 180° C.).

Workup

  1. temperatureAfter refluxing for 2 hours
  2. customThe solvent was then removed
  3. additionthe residue was poured into ice-water which
  4. customprecipitated a yellow solid
  5. customAfter recrystallization from methanol
  6. customthe pure compound was obtained in 30% yield as yellow needles (0.7 grams; m.p. 180° C.)

Sources & evidence

ORD record
ord-f3f9f58a21cd44e4a995890184cc5f8a
Source dataset
uspto-grants-1989_11
Patent number
US04882261

Reaction notes

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