Water → Methyl 5-(benzyloxy)-6-chloronicotinate

HRID 709795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 709795
[Cl:1][C:2]1[C:11]([OH:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[CH2:15]([O:12][C:11]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 46941479Methyl 6-chloro-5-hydroxynicotinate

Produkt 1

HCID 71496987Methyl 5-(benzyloxy)-6-chloronicotinateAusbeute 38,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of methyl 6-chloro-5-hydroxynicotinate (10.5 g) in DMF (80 mL) was added 60% sodium hydride (2.80 g) at 0° C., and the mixture was stirred at 0° C. for 0.5 hr. Benzyl bromide (10.5 g) was added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was poured into water, and the precipitate was collected by filtration. The crude crystals were purified by silica gel column chromatography (petroleum ether/THF) to give the title compound (6.00 g) as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 20 hr
  2. filtrationthe precipitate was collected by filtration
  3. customThe crude crystals were purified by silica gel column chromatography (petroleum ether/THF)

Quellen und Nachweise

ORD-Eintrag
ord-dfd1e4923bb4438c84b11435905ef818
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181186B2

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