2,6-Bis(chloromethyl)pyridine → 1H-Isoindole-1,3(2H)-dione, 2-[[6-(chloromethyl)-2-pyridinyl]methyl]-

HRID 1258576

Reaktionsgleichung

Reaktionsgleichung von HRID 1258576
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][Cl:10])[N:4]=1.[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K]>CN(C=O)C>[Cl:10][CH2:9][C:5]1[N:4]=[C:3]([CH2:2][N:15]2[C:11](=[O:21])[C:12]3[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:14]2=[O:16])[CH:8]=[CH:7][CH:6]=1

Komponenten

4

Edukt 2

HCID 3166542,6-Bis(chloromethyl)pyridineHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 666711941H-Isoindole-1,3(2H)-dione, 2-[[6-(chloromethyl)-2-pyridinyl]methyl]-Ausbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2,6-bis(chloromethyl)pyridine (20 g, 113.6 mmol, 1 eq.) in 250 ml of DMF was added potassium phthalimide (21.04 g, 113.6 mmol, 1 eq.). The reaction was stirred at r.t. overnight then the solvent was evaporated and the residue taken in EtOAc. The insolubles were removed by filtration and the filtrate washed with H2O. The organic layer was separated, dried over MgSO4 and concentrated. The resulting white solid was recrystallised from IPE/EtOAc (1/1) to give 2-{[6-(chloromethyl)pyridin-2-yl]methyl}-1H-isoindole-1,3(2H)-dione (22.34 g, 68% yield) as a white solid.

Aufarbeitung

  1. customthe solvent was evaporated
  2. customThe insolubles were removed by filtration
  3. washthe filtrate washed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe resulting white solid was recrystallised from IPE/EtOAc (1/1)

Quellen und Nachweise

ORD-Eintrag
ord-349f004a71d94e8d92cdcdcfb64a611c
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466176B2

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