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

HRID 1860904Notes

Reaction equation

HRID 1860904 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.[CH3:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[CH2:20][C:21](=[O:27])[NH:22]2.N1CCCCC1.C(O)(=O)C>C(O)C>[CH3:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[C:20](=[CH:1][C:3]1[NH:4][C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=3[C:11]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[C:21](=[O:27])[NH:22]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 106090023-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acidHCID 125793824-Methyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 697651673-[2-(4-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acidYield 81.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (5.4 g), 3.2 g of 4-methyl-2-oxindole and 2.7 g of piperidine 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 in 30 mL of refluxing ethanol, cooled, collected by vacuum filtration, washed with 30 mL of ethanol and dried under vacuum to give 6.2 g (80% yield) of 3-[2-(4-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid as an orange solid.

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 in 30 mL of refluxing ethanol
  7. temperaturecooled
  8. filtrationcollected by vacuum filtration
  9. washwashed with 30 mL of ethanol
  10. customdried under vacuum

Sources & evidence

ORD record
ord-99c1c390b1d34defbdb6008c5607d9bf
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

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