Pyrrolidine → HCID 86644169, compound

HRID 2078396Notes

Reaction equation

HRID 2078396 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:28])[C:15]([O:18][C:19]1[C:24]([CH:25]=O)=[CH:23][C:22]([Cl:27])=[CH:21][N:20]=1)([CH3:17])[CH3:16].N1CCCC1>CO>[CH3:12][O:13][C:14](=[O:28])[C:15]([O:18][C:19]1[C:24](/[CH:25]=[C:6]2\[C:7](=[O:11])[NH:8][C:9]3[C:5]\2=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=3)=[CH:23][C:22]([Cl:27])=[CH:21][N:20]=1)([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 59443772HCID 59443772, compound

Product 1

HCID 86644169HCID 86644169, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To the mixture of 6-chlorooxindole (4.9 g, 29.3 mmol) and 2-(5-Chloro-3-formyl-pyridin-2-yloxy)-2-methyl-propionic acid methyl ester (7.2 g, 28 mmol) in methanol (50 mL) was added pyrrolidine (2.3 mL, 28 mmol) dropwise. The mixture was then heated at 70° C. for 1 h. After cooled to room temperature, the mixture was filtered and the precipitate was collected, dried to give title compound as a yellow solid (9 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-e4f02f13eeea41328762b288ace9aeb0
Source dataset
uspto-grants-2011_04
Patent number
US07928233B2

Reaction notes

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