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

HRID 658913Notes

Reaction equation

HRID 658913 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH3:12][O:13][C:14](=[O:30])[C:15]([O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[CH:28]=O)([CH2:18][CH3:19])[CH2:16][CH3:17].N1CCCC1>CO>[CH3:12][O:13][C:14](=[O:30])[C:15]([O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1/[CH:28]=[C:6]1\[C:7](=[O:11])[NH:8][C:9]2[C:5]\1=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)([CH2:16][CH3:17])[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 594280992-(4-Chloro-2-formyl-phenoxy)-2-ethyl-butyric acid methyl ester

Product 1

HCID 86632088Z-2-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-ethyl-butyric acid methyl esterYield 77.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To the mixture of 6-chlorooxindole (8.3 g, 49.7 mmol) and 2-(4-chloro-2-formyl-phenoxy)-2-ethyl-butyric acid methyl ester (13 g, 45.8 mmol) in methanol (200 mL) was added pyrrolidine (4.1 mL, 49.7 mmol) dropwise. The mixture was then heated at 70° C. for 2 h. After cooled to room temperature, the mixture was filtered and the precipitate was collected, dried to give the title compound as a yellow solid (15.5 g).

Workup

  1. temperatureAfter cooled to room temperature
  2. filtrationthe mixture was filtered
  3. customthe precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-35095cf2172d4526838d10ada217c107
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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