Pyrrolidine → HCID 86617595, compound

HRID 1728165Notes

Reaction equation

HRID 1728165 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]([CH3:13])[CH3:12])=[C:6]([CH:9]=1)[CH:7]=O.[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([CH2:19][C:20](=[O:24])[NH:21]2)=[CH:17][CH:16]=1.N1CCCC1>CO>[Cl:14][C:15]1[CH:23]=[C:22]2[C:18](/[C:19](=[CH:7]/[C:6]3[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:10][CH:11]([CH3:13])[CH3:12])/[C:20](=[O:24])[NH:21]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 51996155-chloro-2-isopropoxybenzaldehyde

Product 1

HCID 86617595HCID 86617595, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

5-Chloro-2-isopropoxy-benzaldehyde (3 g, 15.1 mmol) and 6-chlorooxindole (2 g, 12.6 mmol) were mixed in anhydrous methanol (30 mL) at room temperature. Then pyrrolidine (1.07 g, 15.1 mmol) was added slowly. The reaction mixture was heated at 70° C. for 3 h. Then the mixture was cooled to room temperature and filtered. The precipitate was dried and collected to give E/Z-6-chloro-3-(5-chloro-2-isopropoxy-benzylidene)-1,3-dihydro-indol-2-one as a yellow solid (3.4 g).

Workup

  1. temperatureThen the mixture was cooled to room temperature
  2. filtrationfiltered
  3. customThe precipitate was dried
  4. customcollected

Sources & evidence

ORD record
ord-181d317332c14686ac4859351d4f54f5
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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