Pyrrolidine → HCID 86760830, compound

HRID 1728203Notes

Reaction equation

HRID 1728203 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[CH:7]=O.[Cl:11][C:12]1[CH:20]=[C:19]2[C:15]([CH2:16][C:17](=[O:21])[NH:18]2)=[CH:14][CH:13]=1.N1CCCC1>CO>[Cl:11][C:12]1[CH:20]=[C:19]2[C:15](/[C:16](=[CH:7]/[C:6]3[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[CH3:10])/[C:17](=[O:21])[NH:18]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 123475655-Chloro-2-methylbenzaldehyde

Product 1

HCID 86760830HCID 86760830, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

5-Chloro-2-methyl-benzaldehyde (4 g, 16 mmol) and 6-chlorooxindole (2.5 g, 16 mmol) were mixed in anhydrous methanol (20 mL). Then pyrrolidine (1.32 mL, 16 mmol) was added slowly at r.t. The mixture was heated to 70° C. for 3 h and cooled to room temperature. The precipitate was collected by filtration to give title compound as yellow solid (Yield: 4.5 g).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4d80cdbda84f4f29b1db794d30d6a07e
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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