Pyrrolidine → HCID 86632076, compound

HRID 504538Notes

Reaction equation

HRID 504538 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.[Cl:12][C:13]1[CH:22]=[CH:21][C:16]([O:17][CH2:18][C:19]#[N:20])=[C:15]([CH:23]=O)[CH:14]=1.N1CCCC1>CO>[Cl:12][C:13]1[CH:22]=[CH:21][C:16]([O:17][CH2:18][C:19]#[N:20])=[C:15](/[CH:23]=[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:14]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 4767035HCID 4767035, compound

Product 1

HCID 86632076HCID 86632076, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To the mixture of 6-chlorooxindole (18.4 g, 0.110 mol) and (4-chloro-2-formyl-phenoxy)-acetonitrile (21.5 g, 0.110 mol) in methanol (200 mL) was added pyrrolidine (8.60 g, 0.121 mol) dropwise. Then the mixture was heated at 70° C. for 2 h. After cooled to room temperature, the mixture was filtered. The precipitate was collected and dried to give the title compound as a yellow solid (8.5 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-7b2d2d6ad0d14e26809963cd8f34c921
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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