Chloromethylphthalimide → 4-(Phthalimidomethyloxy)pyridine

HRID 863966

Reaktionsgleichung

Reaktionsgleichung von HRID 863966
[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]>COCCOC>[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 80711,2-DimethoxyethaneLösungsmittel

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 DME, 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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-dc9ef8eaa5f543ff852e77e165e07368
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05561147

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