2-Pyridinecarboxaldehyde → 5-Chloro-3-[(pyridin-2-yl)methylidene]-1,3-dihydro-2H-indol-2-one

HRID 1271405Notes

Reaction equation

HRID 1271405 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=O>N1CCCCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1

Participants

5

Reactant 2

HCID 142732-PyridinecarboxaldehydeHCID 1528015-Chlorooxindole

Product 1

HCID 694911725-Chloro-3-[(pyridin-2-yl)methylidene]-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A 5 mL of ethanol solution containing 5-chlorooxindole (167 mg, 1 mmol), 2-pyridine-carboxaldehyde (129 mg, 1.2 mmol) and 3 drops of piperidine was stirred at 80° C. for 6 hours. After cooling the solution to 5° C., yellow precipitate was obtained (200 mg, 78%). MS: m/z 257 [M+1]+.

Workup

  1. temperatureAfter cooling the solution to 5° C.
  2. customyellow precipitate was obtained (200 mg, 78%)

Sources & evidence

ORD record
ord-b836a762aa1b4b55aeb7ccfbfc2f421b
Source dataset
uspto-grants-2007_04
Patent number
US07205328B2

Reaction notes

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