Isatin → 3-(3,4-dichloroanilino)indol-2-one

HRID 1374967Notes

Reaction equation

HRID 1374967 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=O)[C:2]1=[O:11].[Cl:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[Cl:20])[NH2:16]>>[Cl:12][C:13]1[CH:14]=[C:15]([N:16]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:11])[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

3

Reactant 2

HCID 7054IsatinHCID 72573,4-Dichloroaniline

Product 1

HCID 1355442433-(3,4-dichloroanilino)indol-2-oneYield 95.2%

Conditions

Temperature
75 °C

Procedure

A mixture of 1H-indole-2,3-dione (10.3 g, 70 mmol), 3,4-dichloroaniline (17.0 g, 70 mmol) was heated at 75° C. for 2 hours in a tightly sealed round bottom flask under argon and cooled to room temperature. The solid was recrystallized from CH2Cl2, giving the desired product (19.4 g, 90%).

Workup

  1. temperaturecooled to room temperature
  2. customThe solid was recrystallized from CH2Cl2

Sources & evidence

ORD record
ord-e37ba73ffbfb4eeb8a91406ce9ef5858
Source dataset
uspto-grants-2007_01
Patent number
US07166635B2

Reaction notes

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