Pyrrolidine → HCID 68956475, compound

HRID 658934Notes

Reaction equation

HRID 658934 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]([C:16]1([O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[CH:28]=O)[CH2:19][CH2:18][CH2:17]1)=[O:15].N1CCCC1>CO>[CH3:12][O:13][C:14]([C:16]1([O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2/[CH:28]=[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)[CH2:19][CH2:18][CH2:17]1)=[O:15]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 57565924HCID 57565924, compound

Product 1

HCID 68956475HCID 68956475, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To the mixture of 6-chlorooxindole (10 g, 60 mmol) and 1-(4-chloro-2-formyl-phenoxy)-cyclobutanecarboxylic acid methyl ester (18 g, 67 mmol) in methanol (100 mL) was added pyrrolidine (4.5 mg, 63 mmol) dropwise. The mixture was then heated at 80° C. for 1 h. After cooled to room temperature, the mixture was filtered and the precipitate was collected, dried to give the title compound (6 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-5a7f826094cc4dee989b7dcb24f11184
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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