Pyrrolidine → HCID 86643685, compound

HRID 658904Notes

Reaction equation

HRID 658904 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[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[CH:26]=O)([CH3:17])[CH3:16].N1CCCC1>CO>[CH3:12][O:13][C:14](=[O:28])[C:15]([O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1/[CH:26]=[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)([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 59549299HCID 59549299, compound

Product 1

HCID 86643685HCID 86643685, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To the mixture of 6-chloro-1,3-dihydro-indol-2-one (43 g, 0.26 mol) and 2-(4-chloro-2-formyl-phenoxy)-2-methyl-propionic acid methyl ester (66 g, 0.26 mol) in methanol (700 mL) was added pyrrolidine (22 g, 0.31 mol) dropwise. The mixture was then heated at 70° 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 (76 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-e8c9e647dab340a2821725ae69d50acc
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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