Ammonia → 3-[2-(2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionamide

HRID 24512Notes

Reaction equation

HRID 24512 reaction equation
[O:1]=[C:2]1[C:10](=[CH:11][C:12]2[NH:13][C:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=3[C:20]=2[CH2:21][CH2:22][C:23]([OH:25])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(N1C=CN=C1)([N:28]1C=CN=C1)=O.N.O>CN(C)C=O>[O:1]=[C:2]1[C:10](=[CH:11][C:12]2[NH:13][C:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=3[C:20]=2[CH2:21][CH2:22][C:23]([NH2:28])=[O:25])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 541237443-[2-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid

Product 1

HCID 697653763-[2-(2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionamideYield 110.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-[2-(2-Oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid (10 g) was dissolved in 100 mL of dimethylformamide. Carbonyldiimidazole (6.3 g) was added and the mixture stirred at ambient temperature for 1 hour. Ammonia (1 g) in 30 mL of dimethylformamide was added and the stirring continued overnight. Fifty mL of water was added to the mixture and stirring was continued for 10 minutes. The precipitate that formed was collected by vacuum filtration, washed with 20 mL of water and then 20 mL of ethanol. The solid was slurry-washed with 30 mL of refluxing ethanol for 5 minutes and cooled to room temperature. The solid was collected by vacuum filtration, washed with 20 mL of ethanol and vacuum dried to give 11 g (83% yield) of 3-[2-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionamide.

Workup

  1. customthe stirring continued overnight
  2. stirringstirring
  3. waitwas continued for 10 minutes
  4. customThe precipitate that formed
  5. filtrationwas collected by vacuum filtration
  6. washwashed with 20 mL of water
  7. washThe solid was slurry-washed with 30 mL of refluxing ethanol for 5 minutes
  8. temperaturecooled to room temperature
  9. filtrationThe solid was collected by vacuum filtration
  10. washwashed with 20 mL of ethanol and vacuum
  11. customdried

Sources & evidence

ORD record
ord-f94717ceca3145e18eeddb0ef7559450
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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