Water → HCID 57025073, compound

HRID 1060771Notes

Reaction equation

HRID 1060771 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:21].N1CCCCC1.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:14]1[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:12][C:13]1=[O:21])[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 1425995-Chloro-1-indanoneHCID 321710Oxindole

Product 1

HCID 57025073HCID 57025073, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 500 mg 5-chloro-1-indanone, 1.33 g oxindole and 0.5 ml piperidine in 3 ml dimethylforamide was heated in a sealed tube at 95° C. overnight. Water was added to the reaction mixture to yield an oily solid. The mixture was sonicated for a few minutes then decanted. This washing procedure was repeated several times. The solid was then filtered and washed with ethyl acetate/hexanes (1:3) to yield 172 mg of 3-(5-chloroindan-1-ylidene)-1,3-dihydroindol-2-one as a mustard colored solid.

Workup

  1. customto yield an oily solid
  2. customThe mixture was sonicated for a few minutes
  3. customthen decanted
  4. filtrationThe solid was then filtered
  5. washwashed with ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-ab95ed83efed4022adb0ef9e6856ac3d
Source dataset
uspto-grants-2003_02
Patent number
US06525072B1

Reaction notes

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