Pyrrolidine → HCID 86760824, compound

HRID 1728195Notes

Reaction equation

HRID 1728195 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])=[C:6]([CH:9]=1)[CH:7]=O.[Cl:17][C:18]1[CH:26]=[C:25]2[C:21]([CH2:22][C:23](=[O:27])[NH:24]2)=[CH:20][CH:19]=1.N1CCCC1>CO>[Cl:17][C:18]1[CH:26]=[C:25]2[C:21](/[C:22](=[CH:7]/[C:6]3[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:10][CH2:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])/[C:23](=[O:27])[NH:24]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 57565970HCID 57565970, compound

Product 1

HCID 86760824HCID 86760824, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

5-Chloro-2-(3-hydroxy-2,2-dimethyl-propoxy)-benzaldehyde (2.4 g, 10 mmol) and 6-chloro-1,3-dihydro-indol-2-one (1.7 g, 10 mmol) were mixed in anhydrous methanol (20 mL). Then pyrrolidine (0.8 g, 11.2 mmol) was added slowly at r.t. The mixture was heated to 70° C. for 3 h and cooled to room temperature. Then the precipitate was collected by filtration to give title compound as yellow solid (Yield: 3.8 g).

Workup

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

Sources & evidence

ORD record
ord-38afd99ae85640b993a8e3d57bbf329d
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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