Methyl cyanoacetate → methyl (2Z)-cyano[2-oxo-5-(trifluoromethoxy)-1,2-dihydro-3H-indol-3-ylidene]acetate

HRID 883640

Reaction equation

[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=O.[C:17]([CH2:19][C:20]([O:22][CH3:23])=[O:21])#[N:18]>>[C:17](/[C:19](=[C:7]1/[C:8](=[O:13])[NH:9][C:10]2[C:6]/1=[CH:5][C:4]([O:3][C:2]([F:16])([F:15])[F:1])=[CH:12][CH:11]=2)/[C:20]([O:22][CH3:23])=[O:21])#[N:18]

Participants

Reactant 2

HCID 7747Methyl cyanoacetate

HCID 27327525-(trifluoromethoxy)-2,3-dihydro-1H-indole-2,3-dione

Product 1

HCID 67424559methyl (2Z)-cyano[2-oxo-5-(trifluoromethoxy)-1,2-dihydro-3H-indol-3-ylidene]acetateYield 77%

Procedure

Following the general method as outlined for Intermediate 1, starting from 5-(trifluoromethoxy)-isatin and methyl cyanoacetate, the title compound was isolated, after evaporation, as a dark purple solid in 77% yield. This was a 7.5:1 mixture of geometric isomers.

Sources & evidence

ORD record: ord-0b8386fe95eb4640b6b24d51e763efa5
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236963B2

Linked notes

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