Pyrrolidine → Z-3-[4-Chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2,2-dimethyl-propionic acid methyl ester

HRID 504476Notes

Reaction equation

HRID 504476 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]([CH3:17])([CH3:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[CH:14]=O.[Cl:19][C:20]1[CH:28]=[C:27]2[C:23]([CH2:24][C:25](=[O:29])[NH:26]2)=[CH:22][CH:21]=1.N1CCCC1>CO>[CH3:1][O:2][C:3](=[O:18])[C:4]([CH3:17])([CH3:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1/[CH:14]=[C:24]1\[C:25](=[O:29])[NH:26][C:27]2[C:23]\1=[CH:22][CH:21]=[C:20]([Cl:19])[CH:28]=2

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 575660603-(4-Chloro-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl ester

Product 1

HCID 86632059Z-3-[4-Chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2,2-dimethyl-propionic acid methyl esterYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

3-(4-chloro-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl ester (6.7 g, 25 mmol) and 6-Chloro-1,3-dihydro-indol-2-one (4.35 g, 25 mmol) were mixed in 20 mL of anhydrous methanol. Then pyrrolidine (2 mL, 25 mmol) was added dropwise at r.t. The mixture was heated to 70° C. for 3 h and cooled to room temperature. The precipitate was collected by filtration and dried to give title compound as yellow solid (Yield: 7 g, 67%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-63d5b61cc250479a81f31ef831c38b52
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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