Phthalaldehyde → 2-(4-acetylphenyl)isoindolin-1-one

HRID 703203Notes

Reaction equation

HRID 703203 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH:13]1[CH:18]=[C:17](C=O)[C:16]([CH:21]=O)=[CH:15][CH:14]=1.C(Cl)Cl>CO>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:21][C:16]3[C:15](=[CH:14][CH:13]=[CH:18][CH:17]=3)[C:11]2=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 4807PhthalaldehydeHCID 6344DichloromethaneHCID 994524-Acetylphenyl isocyanate

Product 1

HCID 9108492-(4-acetylphenyl)isoindolin-1-oneYield 42.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-acetylphenylisocyanate (27.5 g, 0.17 mol) and o-phthalicdicarboxaldehyde (25.0 g, 0.186 mol) is heated in an oil bath at 170°-175° C. for 4.0 hours under nitrogen atmosphere. On cooling the melt solidified which is pulverized and refluxed with CH2Cl2 and CH3OH and filtered to give 18.2 g (41.4%) of the desired 2-(4-acetylphenyl)-2,3-dihydro-1H-isoindole-1-one, mp 235°-237° C. The residue is recrystallized from DMF (1800 ml). Yield 13.0 g (29.6%), mp 236-239° C. (Jap. patent J5 7050-960; mp 243°-244° C. for the nonsolvated compound, prepared by a different route).

Workup

  1. temperatureis heated in an oil bath at 170°-175° C. for 4.0 hours under nitrogen atmosphere
  2. temperatureOn cooling the melt
  3. filtrationfiltered

Sources & evidence

ORD record
ord-262c93ec86e14cd09b5f4809b80e9178
Source dataset
uspto-grants-1991_01
Patent number
US04981865

Reaction notes

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