1,5,6,7-Tetrahydro-4H-indol-4-one → HCID 69941588, compound

HRID 478718Notes

Reaction equation

HRID 478718 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=O)[C:4]=2[CH:3]=[CH:2]1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][C:12]1=[O:20]>CN(C)C=O.O>[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[C:5]2[CH2:6][CH2:7][CH2:8][C:9]3[NH:1][CH:2]=[CH:3][C:4]2=3)[C:12]1=[O:20]

Participants

5

Reactant 2

HCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneHCID 321710Oxindole

Product 1

HCID 69941588HCID 69941588, compoundYield 11.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 680 mg 1,5,6,7-tetrahydro-4H-indol-4-one and 1.33 g oxindole in 3 ml dimethylforamide was heated at 140° C. for 50 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed with water and then brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified on a silica gel column using hexanes/ethyl acetate as the eluent to provide 150 mg of 1′,5′,6′,7′-tetrahydro-1H-[3,4′]biindolyliden-2-one as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with water
  3. dry with materialbrine, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified on a silica gel column

Sources & evidence

ORD record
ord-5f675d795f414d118c5fae95926f074e
Source dataset
uspto-grants-2003_11
Patent number
US06642251B1

Reaction notes

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