Chloromethylphthalimide → 4-(Phthalimidomethyloxy)pyridine

HRID 964101

Reaktionsgleichung

Reaktionsgleichung von HRID 964101
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Cl[CH2:9][N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20]>CN(C=O)C>[C:11]1(=[O:20])[N:10]([CH2:9][O:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]12

Komponenten

4

Edukt 2

HCID 87154ChloromethylphthalimideHCID 178418642HCID 178418642, Verbindung

Produkt 1

HCID 190791054-(Phthalimidomethyloxy)pyridineAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4.76 g (50 mmol) of 4-hydroxypyridine and 10.76 g (55 mmol) of N-chloromethylphthalimide. in 80 ml of DMF, 8.23 ml (55 mmol) of 1,8-diazabicyclo[5,4,0]-2-undecene was added. The mixture was stirred at room temperature for. 2 hours. After the solvent was distilled off, the reaction mixture was poured into water and extracted with ethyl acetate. The precipitate was filtered off. The aqueous layer was further extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 2.67 g of the desired compound (yield: 21%, colorless crystals). mp: 129.0°-131.0° C.

Aufarbeitung

  1. custom2 hours
  2. distillationAfter the solvent was distilled off
  3. additionthe reaction mixture was poured into water
  4. extractionextracted with ethyl acetate
  5. filtrationThe precipitate was filtered off
  6. extractionThe aqueous layer was further extracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ecaba718089a4ea3a6b472e1ac919e0d
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05767121

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