Pyrrolidine → HCID 86760828, compound

HRID 1728202

Reaction equation

HRID 1728202 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][CH2:13][OH:14])=[C:6]([CH:9]=1)[CH:7]=O.[Cl:15][C:16]1[CH:24]=[C:23]2[C:19]([CH2:20][C:21](=[O:25])[NH:22]2)=[CH:18][CH:17]=1.N1CCCC1>CO>[Cl:15][C:16]1[CH:24]=[C:23]2[C:19](/[C:20](=[CH:7]/[C:6]3[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:10][CH2:11][CH2:12][CH2:13][OH:14])/[C:21](=[O:25])[NH:22]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 575659355-Chloro-2-(3-hydroxy-propoxy)-benzaldehyde

Product 1

HCID 86760828HCID 86760828, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

5-Chloro-2-(3-hydroxy-1-propoxy)-benzaldehyde (8 g, 37 mmol) and 6-chlorooxindole (6.2 g, 37 mmol) were mixed in anhydrous methanol (20 mL). Then pyrrolidine (3 mL, 37 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 a yellow solid (Yield: 11.8 g).

Workup

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

Sources & evidence

ORD record
ord-438e668c95e447499ba8cdc223373e7b
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Linked notes

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