Pyrrolidine → 6-Chloro-3-(5-chloro-pyridine-3-ylmethylene)-1,3-dihydro-indol-2-one

HRID 1728190Notes

Reaction equation

HRID 1728190 reaction equation
ClC1C=C2C(CC(=O)N2)=CC=1.ClC1C=C(C=O)C=NC=1.N1CCCC1.[Cl:26][C:27]1[CH:35]=[C:34]2[C:30](/[C:31](=[CH:37]/[C:38]3[CH:39]=[N:40][CH:41]=[C:42]([Cl:44])[CH:43]=3)/[C:32](=[O:36])[NH:33]2)=[CH:29][CH:28]=1>CO>[Cl:26][C:27]1[CH:35]=[C:34]2[C:30]([C:31](=[CH:37][C:38]3[CH:39]=[N:40][CH:41]=[C:42]([Cl:44])[CH:43]=3)[C:32](=[O:36])[NH:33]2)=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 144441965-Chloro-pyridine-3-carbaldehydeHCID 68956604Z-6-chloro-3-(5-chloro-pyridine-3-ylmethylene)-1,3-dihydro-indol-2-one

Product 1

HCID 689566056-Chloro-3-(5-chloro-pyridine-3-ylmethylene)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To the mixture of 6-chlorooxindole (0.93 g, 5.6 mmol) and 5-chloro-pyridine-3-carbaldehyde (0.8 g, 5.6 mmol) in methanol (10 mL) was added pyrrolidine (0.6 g, 5.6 mmol) dropwise. The mixture was then heated at 70° C. for 3 h and cooled to room temperature. The precipitate was collected, dried to give a mixture of E/Z-6-chloro-3-(5-chloro-pyridine-3-ylmethylene)-1,3-dihydro-indol-2-one as a bright yellow solid (Yield 1.0 g, 63%).

Workup

  1. temperaturecooled to room temperature
  2. customThe precipitate was collected
  3. customdried
  4. customto give

Sources & evidence

ORD record
ord-3c636d0d8f7249faae9abea1b1efb620
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

Loading…