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

HRID 616781Notes

Reaction equation

HRID 616781 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]1[CH3:20])[CH2:9][CH3:10]>C1C=CC=CC=1>[CH2:8]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:3]([CH2:2][C:1]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]([CH2:8][CH2:9][CH3:10])[C:12]=2[CH3:20])=[O:7])[C:4]([OH:6])=[O:5])=[C:12]1[CH3:20])[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 51481481-n-Propyl-2-methylindole

Product 1

HCID 541106242,4-Bis(1-n-propyl-2-methyl-3-indolyl)-4-oxobutanoic acidYield 33.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of 20.0 g (0.204 mole) of maleic anhydride and 70.0 g (0.408 mole) of 1-n-propyl-2-methylindole in 200 ml of benzene was heated at reflux for a period of approximately eighteen hours and then allowed to cool to ambient temperature. The solid which separated from the cooled solution was collected by filtration, washed with fresh chilled benzene and dried in vacuo at 60° C to obtain 30.0 g of 2,4-bis(1-n-propyl-2-methyl-3-indolyl)-4-oxobutanoic acid (Formula VII: R=CH3CH2CH2 ; R1 =CH3 ; Y=H) as a white solid melting over the range 210° to 215° C.

Workup

  1. temperatureat reflux for a period of approximately eighteen hours
  2. customThe solid which separated from the cooled solution
  3. filtrationwas collected by filtration
  4. washwashed
  5. temperaturewith fresh chilled benzene
  6. customdried in vacuo at 60° C

Sources & evidence

ORD record
ord-1b623068cfa649e6aa31e562df803f47
Source dataset
uspto-grants-1978_02
Patent number
US04075224

Reaction notes

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