5-chloro-1H-indole-2,3-dione → 5-chloro-3-hydroxy-3-(2-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-one

HRID 1662691Notes

Reaction equation

HRID 1662691 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2=[O:22]>>[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2([OH:22])[C:2]1[CH:3]=[C:4]([CH3:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

3

Reactant 2

HCID 872035-chloro-1H-indole-2,3-dioneHCID 891432-Bromo-4-methylanisole

Product 1

HCID 674294775-chloro-3-hydroxy-3-(2-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-oneYield 90.8%

Procedure

With 4.36 g of 3-bromo-4-methoxy toluene and 2.81 g of 5-chloroisatin as starting materials, 4.27 g of the title compound (light brown solid) was obtained by a similar method to Step 21-1.

Sources & evidence

ORD record
ord-3cc28030a37a421385a3baaf3738b93a
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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