1,2-Dimethylindole → 4-(1,2-Dimethyl-3-indolyl)-2,3-dichloro-4-oxo-2-butenoic acid

HRID 1632888Notes

Reaction equation

HRID 1632888 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH3:11].[Cl:12][C:13]1=[C:14]([Cl:20])[C:15]([O:17][C:18]1=[O:19])=[O:16]>C(Cl)CCl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:15](=[O:16])[C:14]([Cl:20])=[C:13]([Cl:12])[C:18]([OH:19])=[O:17])=[C:3]1[CH3:11]

Participants

4

Reactant 2

HCID 134081,2-DimethylindoleHCID 70728Dichloromaleic anhydride

Product 1

HCID 2362024-(1,2-Dimethyl-3-indolyl)-2,3-dichloro-4-oxo-2-butenoic acidYield 91.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 10.0 g (0.07 mole) of 1,2-dimethylindole, 12.0 g (0.07 mole) of dichloromaleic anhydride and 200 ml of ethylene dichloride was stirred at ambient temperature for approximately eighteen hours. The solid present in the reaction mixture was collected by filtration. After drying at 60° C. in vacuo there was obtained 20.0 g of 4-(1,2-dimethyl-3-indolyl)-2,3-dichloro-4-oxo-2-butenoic acid (Formula VIII: R=R1 =CH3 ; Y=H) as a pale blue solid which melted over the range 150° to 153° C. Infrared spectral analysis showed a maximum at 1712 (C=0; s) cm-1.

Workup

  1. filtrationThe solid present in the reaction mixture was collected by filtration
  2. customAfter drying at 60° C. in vacuo

Sources & evidence

ORD record
ord-ca53f09abe594f30aa46f740eb300ec3
Source dataset
uspto-grants-1984_10
Patent number
US04477676

Reaction notes

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