Pyrrolidine → HCID 86632058, compound

HRID 504472Notes

Reaction equation

HRID 504472 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:14]=[CH:15][C:16]([O:21][C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[C:17]([CH:20]=1)[CH:18]=O.N1CCCC1>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:18]/[C:17]3[CH:20]=[C:13]([Cl:12])[CH:14]=[CH:15][C:16]=3[O:21][C:22]3[N:23]=[CH:24][CH:25]=[CH:26][N:27]=3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 57750104HCID 57750104, compound

Product 1

HCID 86632058HCID 86632058, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 6-chlorooxindole (1.1 g, 6.4 mmol) and 5-chloro-2-(pyrimidin-2-yloxy)-benzaldehyde (1.5 g, 6.4 mmol) in methanol (10 mL) was added pyrrolidine (0.5 mL, 6.4 mmol) dropwise. The mixture was then heated at 70° C. for 3 h. After cooled to 4° C., the mixture was filtered and the precipitate was collected, dried to give the title compound as a bright yellow solid (1.3 g).

Workup

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

Sources & evidence

ORD record
ord-e9025830f63c46b4b08da9dc82a3e886
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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