Pyrrolidine → HCID 86760820, compound

HRID 1728168Notes

Reaction equation

HRID 1728168 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][CH2:8][O:9]C(=O)C)=[C:4]([CH:15]=O)[CH:3]=1.[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:15]/[C:4]3[CH:3]=[C:2]([Cl:1])[CH:14]=[CH:13][C:5]=3[O:6][CH2:7][CH2:8][OH:9])/[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 57565950HCID 57565950, compound

Product 1

HCID 86760820HCID 86760820, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Acetic acid 2-(4-chloro-2-formyl-phenoxy)-ethyl ester (1.5 g, 9.3 mmol) and 6-chlorooxindole (2.7 g, 11.2 mmol) were mixed in anhydrous methanol (20 mL) at room temperature. Then Pyrrolidine (0.8 g, 11.2 mmol) was added slowly. The reaction mixture was heated at 70° C. for 3 h, then cooled to r.t and the precipitation was collected by filtration to obtain title compound as a yellow solid (1.4 g).

Workup

  1. temperaturecooled
  2. customthe precipitation
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-fa32caf35f1745f185357647852a8e0c
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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