Acetophenone → HCID 23962083, compound

HRID 1623428Notes

Reaction equation

HRID 1623428 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)[CH3:12].N1CCCC1>C1(C)C=CC=CC=1>[C:14]1([C:11](=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])[CH3:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 31268PyrrolidineHCID 321710Oxindole

Product 1

HCID 23962083HCID 23962083, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Oxindole (0.1332 g, 1 mmol) and acetophenone (1.4 ml, 1.2 mmol) were mixed in toluene; then pyrrolidine (0.17 ml, 2 mmol) was added. The mixture refluxed for 3 hand monitored by TLC. When the reaction was finished the solvent was removed under reduced pressure. The residue was separated by flash chromatography column (gradient elution, 10-25% ethyl acetate in petroleum ether) to give 3-(1-phenyl-ethylidene)-1,3-dihydro-indol-2-one as yellow powder (200 mg, 85%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.70 (s, 3H) 5.96 (d, J=7.83 Hz, 1H) 6.51-6.57 (m, 1H) 6.77 (d, J=7.58 Hz, 1H) 7.00-7.10 (m, 1H) 7.30-7.37 (m, 2H) 7.44-7.58 (m, 3H) 10.54 (br. s., 1H). MS calcd. for C16H13NO 235, obsd. (ESI+) [(M+H)+] 236.

Workup

  1. temperatureThe mixture refluxed for 3 hand
  2. customwas removed under reduced pressure
  3. customThe residue was separated by flash chromatography column (gradient elution, 10-25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-e71bdddd9e2f46b884e5b422d748b6c6
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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