Phenylacetone → Oxindole

Reaction equation

N[N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:11].C1(CC(=O)C)C=CC=CC=1>>[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:11]

Participants

Reactant 2

HCID 7678Phenylacetone

HCID 37753661-amino-1,3-dihydro-2H-indol-2-one

Product 1

HCID 321710Oxindole

Procedure

U.S. Pat. Nos. 4,045,576 and 4,126,635 disclose methods for the preparation of 7-benzoylindolin-2-ones. According to one method, 1-aminoindolin-2-one is reacted with a phenylacetone to give a 1-(α-methylphenethylindenimino) indolin-2-one which is cyclized in ethanolic hydrogen chloride to an ethyl α-(2-methyl-3-phenylindol-7-yl)acetate. This indolylester is treated with ozone in acetic acid solution to give an ethyl 2-acetamido-3-benzoylphenylacetate which is hydrolyzed and cyclized in dilute mineral acid to a 7-benzoylindolin-2-one.

Sources & evidence

ORD record: ord-1af7a583fb2c48e7b4214560c751454d
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04221716

Reaction notes

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