Reaktion #51619

Reaktionsgleichung

2-anilino-6-methoxy-quinoxaline

sodium

ethanethiol

phenol

→

powder

2-Anilino-6-quinoxalinol

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture is concentrated
2. 2
   Sonstigepartitioned between EtOAc and H2O/5% tartaric acid such that the pH of the aqueous layer
3. 3
   WaschenThe organic layer is washed with H2O (4×)
4. 4
   Waschenwashed with EtOAc (2×), re-acidified with 5% tartaric acid
5. 5
   Waschenwashed with multiple portions of EtOAc
6. 6
   Waschenwashed with brine
7. 7
   Trocknendried (Na2SO4)
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe resulting solid is chromatographed (50% EtOAc/hexanes)
10. 10
    SonstigeAn analytical sample is obtained
11. 11
    Sonstigeby triturating the product with Et2O

Vorschrift

By the method of Feutrill, G. I.; Mirrington, R. N. Tet. Lett. 1970, 1327; the aryl methyl ether is converted to the phenol derivative. To 2-anilino-6-methoxy-quinoxaline (0.27 g. 1.07 mmol) under argon in DMF is added the sodium salt of ethanethiol (0.19 g, 2 mmol). The reaction mixture is heated to 110° C. overnight. The mixture is concentrated and partitioned between EtOAc and H2O/5% tartaric acid such that the pH of the aqueous layer is approximately 4. The organic layer is washed with H2O (4×), then with 2.5% NaOH (4×). The basic layers combined, washed with EtOAc (2×), re-acidified with 5% tartaric acid, and washed with multiple portions of EtOAc. The organic layers are combined, washed with brine, dried (Na2SO4), and concentrated. The resulting solid is chromatographed (50% EtOAc/hexanes). An analytical sample is obtained by triturating the product with Et2O to provide a yellow powder (m.p. 211-213° C.). Anal. Calcd. for C14H11N3O: C, 70.88; H, 4.67; N, 17.71; Found: C, 70.64; H, 4.85; N, 17.58.

Quelle