p-Aminoacetophenone → HCID 4238068, compound

HRID 451200Notes

Reaction equation

HRID 451200 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)=[O:13].[CH:21]1[CH2:25][CH:24]=[CH:23][CH:22]=1>C(#N)C.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Sc+3]>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[CH:24]3[CH2:25][CH:21]=[CH:22][CH:23]3[C:16]3[CH:15]=[C:14]([C:12](=[O:13])[CH3:11])[CH:19]=[CH:18][C:17]=3[NH:20]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7468p-AminoacetophenoneHCID 7612CyclopentadieneHCID 312444-Methoxybenzaldehyde

Product 1

HCID 4238068HCID 4238068, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6342AcetonitrileSolvent2×

Procedure

4-Methoxybenzaldehyde (0.074 g, 0.5 mmol) and 4-aminoacetophenone (0.068 g 0.5 mmol) were heated to melting in a round bottom flask, then a solution of the catalyst Sc(OTf)3 (0.0248 g, 0.05 mmol, 10 mol %) in anhydrous acetonitrile (0.2 mL) was added to the molten solid, followed by a solution of cyclopentadiene (0.165 g, 2.5 mmol) in acetonitrile (3 mL). The reaction was stirred at rt for 2.30 h. The reaction mixture was concentrated under reduced pressure. The crude material was purified by preparative column chromatography using silica gel (SiO2) eluted with 10% EtOAc/Hexanes to give the product as a colorless solid (0.120 g, 76%).

Workup

  1. customto melting in a round bottom flask
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe crude material was purified by preparative column chromatography
  4. washeluted with 10% EtOAc/Hexanes

Sources & evidence

ORD record
ord-a0f4285dc0fc4a229d544fd8e95366de
Source dataset
uspto-grants-2013_07
Patent number
US08487100B2

Reaction notes

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