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

HRID 1860928Notes

Reaction equation

HRID 1860928 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[CH:12]([CH3:16])C(O)=O)=O.[Cl:17][C:18]1[C:19]([CH3:28])=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[CH2:21]2.N1CCCCC1.[C:35]([OH:38])(=[O:37])C>C(O)C>[Cl:17][C:18]1[C:19]([CH3:28])=[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][CH2:16][C:35]([OH:38])=[O:37]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 103133885-Chloro-4-methylindolin-2-oneHCID 22571120(2-Formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid

Product 1

HCID 697638863-[2-(5-Chloro-4-methyl-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acidYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (2-Formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (5.4 g), 4.0 g of 5-chloro-4-methyl-2-oxindole and 2.7 g of piperidine in 25 mL of ethanol was refluxed for 4 hours. Addition of acetic acid (8 mL) resulted in the formation of a precipitate. 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 with 30 mL of refluxing ethanol, cooled, collected by vacuum filtration, washed with 30 mL of ethanol and vacuum dried to give 6.8 g (80%) of 3-[2-(5-Chloro-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. customresulted in the formation of a precipitate
  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 with 30 mL of refluxing ethanol
  7. temperaturecooled
  8. filtrationcollected by vacuum filtration
  9. washwashed with 30 mL of ethanol and vacuum
  10. customdried

Sources & evidence

ORD record
ord-06d2228107494edb99336dbcae972b8a
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

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