Maleic Anhydride → 2,4-Bis(1-ethyl-2-methyl-3-indolyl)-4-oxobutanoic acid

HRID 544773Notes

Reaction equation

HRID 544773 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[CH3:12])[CH3:2].[C:13]1(=[O:19])[O:18][C:16](=[O:17])[CH:15]=[CH:14]1>C1C=CC=CC=1>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:14]([CH2:15][C:16]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:3]([CH2:1][CH3:2])[C:4]=2[CH3:12])=[O:17])[C:13]([OH:18])=[O:19])=[C:4]1[CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 1704321H-Indole, 1-ethyl-2-methyl-

Product 1

HCID 204427762,4-Bis(1-ethyl-2-methyl-3-indolyl)-4-oxobutanoic acidYield 30.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred mixture of 160.0 g (0.97 mole) of 1-ethyl-2-methylindole (95 percent assay), 40.0 g (0.408 mole) of maleic anhydride and 700 ml of benzene was heated at reflux for a period of approximately eighteen hours and then cooled to ambient temperature. The separated solid was collected by filtration and dried in vacuo at 60° C. to obtain 52.4 g of 2,4-bis(1-ethyl-2-methyl-3-indolyl)-4-oxobutanoic acid (Formula VII: R=CH3CH2 ; R1 =CH3 ; Y=H), a white solid melting over the range of 221°-225° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for a period of approximately eighteen hours
  3. filtrationThe separated solid was collected by filtration
  4. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-ff781812dedd4b7d8e74d43ceaa166dc
Source dataset
uspto-grants-1984_05
Patent number
US04451657

Reaction notes

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