Pyrrolidine → HCID 86632061, compound

HRID 658938Notes

Reaction equation

HRID 658938 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:26])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[CH:24]=O.N1CCCC1>CO>[CH3:12][O:13][C:14](=[O:26])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1/[CH:24]=[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

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 819983HCID 819983, compound

Product 1

HCID 86632061HCID 86632061, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To the mixture of 6-chloro-1,3-dihydro-indol-2-one (10 g, 60 mmol) and (4-chloro-2-formyl-phenoxy)-acetic acid methyl ester (15.2 g, 67 mmol) in methanol (100 mL) was added pyrrolidine (4.5 g, 63 mmol) dropwise. The mixture was then heated at 80° C. for 1 h. After cooled to room temperature, the mixture was filtered and resulting precipitate was collected, dried to give the title compound as a yellow solid (12 g).

Workup

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

Sources & evidence

ORD record
ord-999d5af78f954226b73ccd177181a58d
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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