Hydrochloric Acid → 5-Hydroxy-2-(4-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione

HRID 47101Notes

Reaction equation

HRID 47101 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[OH:9][C:10]1[CH:11]=[C:12]2[C:17](=O)[O:16][C:14](=[O:15])[C:13]2=[CH:19][CH:20]=1.O.Cl>N1C=CC=CC=1>[OH:9][C:10]1[CH:11]=[C:12]2[C:17](=[O:16])[N:7]([C:6]3[CH:5]=[CH:4][C:3]([OH:8])=[CH:2][CH:1]=3)[C:14](=[O:15])[C:13]2=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4034-AminophenolHCID 962WaterHCID 6397475-Hydroxy-1,3-dihydro-2-benzofuran-1,3-dione

Product 1

HCID 197939855-Hydroxy-2-(4-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a stirred dry flask under N2, to a solution of 54.5 g p-aminophenol (0.5 mole) in 500 ml dry pyridine was added over 10 min at room temperature 82.0 g powdered 4-hydroxyphthalic anhydride (0.31 mole) and the mixture refluxed 5 hr. This black solution was cooled, poured into 1500 ml water, acidified with HCl, filtered, washed, and dried. M.P. 302°-304° C. Recrystallization was unnecessary. Yield 104 g, 82%.

Workup

  1. customIn a stirred dry flask under N2
  2. temperaturethe mixture refluxed 5 hr
  3. temperatureThis black solution was cooled
  4. filtrationfiltered
  5. washwashed
  6. customdried
  7. customRecrystallization

Sources & evidence

ORD record
ord-e1e88d5e97574fb88a0afbbe74842a4b
Source dataset
uspto-grants-1979_11
Patent number
US04176223

Reaction notes

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