5,6-Dimethoxyindolin-2-one → HCID 178486553, compound

HRID 47067

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7](=[O:14])[CH2:6]2.[CH:15]([O-])([O-])[O:16]CC>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7](=[O:14])[C:6]2=[CH:15][OH:16]

Participants

Reactant 2

HCID 2229935,6-Dimethoxyindolin-2-one

HCID 53630039Ethylorthoformate

Product 1

HCID 178486553HCID 178486553, compound

Procedure

As illustrated above in Scheme (A), the intermediate, 5,6-dimethoxy oxindole (I) is reacted with ethyl ortho formate (II) to provide 5,6-dimethoxy-3-hydroxymethylene oxindole (III). This oxindole (III) is then reacted with primary or secondary amines in refluxing benzene in the presence of acetic acid or toluene sulfonic acid to yield 5,6-dimethoxy-3-(substituted amino methylene) oxindoles (IV) or (V), respectively.

Sources & evidence

ORD record: ord-0f88a97320c64033b9dbd7dfa764f397
Source dataset: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04176191

Linked notes

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