5-chloro-1H-indole-2,3-dione → 5-chloro-3-hydroxy-3-[2-(methylthio) phenyl]-1,3-dihydro-2H-indol-2-one

HRID 1662768Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH3:9].[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[C:14]2=[O:21]>>[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[C:14]2([OH:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH3:9]

Participants

Reactant 2

HCID 872035-chloro-1H-indole-2,3-dione

HCID 881662-Bromothioanisole

Product 1

HCID 674296695-chloro-3-hydroxy-3-[2-(methylthio) phenyl]-1,3-dihydro-2H-indol-2-oneYield 66.3%

Procedure

With 15.0 g of 1-bromo-2-(methylthio) benzene and 10.3 g of 5-chloroisatin as starting materials, 11.5 g of the title compound (orange red solid) was obtained by a similar method to Step 21-1.

Sources & evidence

ORD record: ord-c0f63b2647144bb5972a8db198c5ebec
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030499B2

Reaction notes

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