Sodium hydride → Methyl 2-(4-(2-quinoxalinyloxy)phenoxy)propanoate

HRID 64574

Reaktionsgleichung

Reaktionsgleichung von HRID 64574
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl[C:20]1[CH:29]=[N:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1>CN(C)C=O.O>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:28]=[CH:29][C:20]=1[O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[CH:13][CH:14]=1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 2389382-ChloroquinoxalineHCID 366926Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 187099Methyl 2-(4-(2-quinoxalinyloxy)phenoxy)propanoateAusbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

In a nitrogen atmosphere, a solution of 5.9 g (0.03 mole) methyl 2-(4-hydroxyphenoxy)propanoate in 20 cc of dimethylformamide was added dropwise at about 15° C. to 1.5 g (0.03 mole) 57% sodium hydride in 20 cc dimethylformamide. When the evolution of hydrogen ceased, 4.9 g (0.03 mole) 2-chloroquinoxaline was added and the reaction mixture was heated at 130° C. for 4 hours. After standing overnight at room temperature, the reaction mixture was poured into about 100 cc of cold water. The precipitated solid was filtered and crystallized from methanol to give 4.2 g of product, m.p. 110°-115°.

Aufarbeitung

  1. filtrationThe precipitated solid was filtered
  2. customcrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-5036b18fc42848cc80ac44354f281d61
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04609396

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