6-(2-Methoxyphenyl)-1,3-dihydroindol-2-one → HCID 53970938, compound

HRID 1860922Notes

Reaction equation

HRID 1860922 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C:14](=[O:18])[NH:15]2)=[CH:11][CH:10]=1.[CH:19]([C:21]1[NH:22][C:23]2[CH2:24][CH2:25][CH2:26][CH2:27][C:28]=2[C:29]=1[CH2:30][CH2:31][C:32]([OH:34])=[O:33])=O>N1CCCCC1.C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[C:16]2[C:12]([C:13](=[CH:19][C:21]3[NH:22][C:23]4[CH2:24][CH2:25][CH2:26][CH2:27][C:28]=4[C:29]=3[CH2:30][CH2:31][C:32]([OH:34])=[O:33])[C:14](=[O:18])[NH:15]2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 105619756-(2-Methoxyphenyl)-1,3-dihydroindol-2-oneHCID 106090023-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid

Product 1

HCID 53970938HCID 53970938, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 103 mg of 6-(2-methoxyphenyl)-2-oxindole, 95 mg of 3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid and piperidine (3 drops) in ethanol (2 mL) was held in a sealed tube at 90° C. for 4 hrs. The reaction mixture was concentrated and acidified with 6 N hydrochloric acid. The precipitate was collected by filtration and washed with water and hexane to give 67 mg of 3-{2-[6-(2-methoxyphenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}-propionic acid as a brown solid (35% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water and hexane

Sources & evidence

ORD record
ord-bb9663745df2442bb8546c0ca2be7cd7
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

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