Acetic Acid → 3-[2-(5-bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid

HRID 24502Notes

Reaction equation

HRID 24502 reaction equation
[CH:1]([C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=O.[Br:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[CH2:21]2.N1CCCC1.C(O)(=O)C>C(O)C>[Br:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[C:21]2=[CH:1][C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 6111935-Bromo-2-oxindoleHCID 106090023-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid

Product 1

HCID 541516003-[2-(5-bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(2-Formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (3.4 g), 2.7 g of 5-bromo-2-oxindole and 1.4 g of pyrrolidine in 25 mL of ethanol was refluxed for 4 hours. Upon slow addition of acetic acid (8 mL), a precipitate formed. The mixture was refluxed for 5 minutes and cooled to ambient temperature. The precipitate was collected by vacuum filtration and washed with 20 mL of ethanol. The solids were slurry-washed by refluxing in 30 mL of ethanol, cooled, collected by vacuum filtration, washed with 30 mL of ethanol and dried under vacuum to give 5.2 g (98% yield) of 3-[2-(5-bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid as a red-orange solid, mp 286-289° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customa precipitate formed
  3. temperatureThe mixture was refluxed for 5 minutes
  4. filtrationThe precipitate was collected by vacuum filtration
  5. washwashed with 20 mL of ethanol
  6. washThe solids were slurry-washed
  7. temperatureby refluxing in 30 mL of ethanol
  8. temperaturecooled
  9. filtrationcollected by vacuum filtration
  10. washwashed with 30 mL of ethanol
  11. customdried under vacuum

Sources & evidence

ORD record
ord-1926950cb7964e66954b9384f3d949ab
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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