Water → HCID 57001382, compound

HRID 478714Notes

Reaction equation

HRID 478714 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][C:12]1=[O:20].N1CCCCC1.O>CN(C)C=O>[C:1]1(=[C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][C:12]2=[O:20])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 119832-IndanoneHCID 321710Oxindole

Product 1

HCID 57001382HCID 57001382, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.4 g indan-2-one, 1.33 g oxindole and 0.5 ml piperidine in 3 ml dimethylforamide was heated in a sealed tube at 130° C. for 60 hours. Enough water was added to cause precipitation of an oily solid. The mixture was decanted and the remaining oily solid heated with 5 ml of ethanol using a heat gun. Upon cooling, the solid was filtered off. The solid was slurried with 3 ml of ethanol and filtered to give 160 mg of 3-indan-1-ylidene-1,3-dihydroindol-2-one as an orange solid.

Workup

  1. customprecipitation of an oily solid
  2. customThe mixture was decanted
  3. temperaturethe remaining oily solid heated with 5 ml of ethanol using a heat gun
  4. temperatureUpon cooling
  5. filtrationthe solid was filtered off
  6. filtrationfiltered

Sources & evidence

ORD record
ord-0905b0fd41ac437fb463402327d3a2c8
Source dataset
uspto-grants-2003_11
Patent number
US06642251B1

Reaction notes

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