6-Phenyl-1,3-dihydro-indol-2-one → 5-[(1,2-Dihydro-2-oxo-6-phenyl-3H-indol-3-ylidene)methyl]-4-methyl-1H-pyrrole-3-propanoic acid

HRID 1937599Notes

Reaction equation

HRID 1937599 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[C:7]([CH3:13])=[C:8]([CH:11]=O)[NH:9][CH:10]=1)([OH:3])=[O:2].[C:14]1([C:20]2[CH:28]=[C:27]3[C:23]([CH2:24][C:25](=[O:29])[NH:26]3)=[CH:22][CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1CCCCC1.C(O)C>[CH3:13][C:7]1[C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])=[CH:10][NH:9][C:8]=1[CH:11]=[C:24]1[C:23]2[C:27](=[CH:28][C:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:21][CH:22]=2)[NH:26][C:25]1=[O:29]

Participants

5

Reactant 2

HCID 105363846-Phenyl-1,3-dihydro-indol-2-oneHCID 151607523-(5-formyl-4-methyl-1H-pyrrol-3-yl)propanoic acid

Product 1

HCID 572379515-[(1,2-Dihydro-2-oxo-6-phenyl-3H-indol-3-ylidene)methyl]-4-methyl-1H-pyrrole-3-propanoic acidYield 78.5%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (90.5 mg), 105 mg 6-phenyl-2-oxindole and 2 drops piperidine in 2 mL of ethanol were heated at 90° C. overnight. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 146 mg (78%) of the title compound as a brown solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. filtrationThe precipitate was filtered
  4. washwashed with water to pH 6
  5. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-f3844300645540d1afee6b4ec9e390dd
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

Loading…