1H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)- → 2-(Phthalimidomethyloxy)pyridine

HRID 964102

Reaktionsgleichung

Reaktionsgleichung von HRID 964102
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[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]>C1C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[C:11]1(=[O:20])[N:10]([CH2:9][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]12

Komponenten

5

Edukt 2

HCID 792441H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)-HCID 178516071HCID 178516071, Verbindung

Produkt 1

HCID 190791522-(Phthalimidomethyloxy)pyridineAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In 4 ml of benzene were suspended 0.095 g (1.0 mmol) of 2-hydroxypyridine and 0.14 g (0.5 mmol) of silver carbonate, N-bromomethylphthalimide [0.29 g (1.2 mmol)] was added at room temperature, and the mixture was stirred at 80° C. for 14 hours under heating. After cooling, the residue was filtered and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate/hexane=10:1) to obtain powder. The powder was recrystallized from ethyl acetate to obtain 0.10 g of the desired compound (yield: 39.0%, colorless columns).

Aufarbeitung

  1. additionwas added at room temperature
  2. temperatureunder heating
  3. temperatureAfter cooling
  4. filtrationthe residue was filtered
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate/hexane=10:1)
  7. customto obtain powder
  8. customThe powder was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0963a453584747558468c369c862f080
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05767121

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