Reaktion #2133092

Reaktionsgleichung

NaOH

2-(3-nitrophenyl)quinoxaline

SnCl2.H2O

→

(3-quinoxalin-2-ylphenyl)amine

Ausbeute 68.0%

Lösungsmittel

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONadding ice as necessary
2. 2
   Temperaturto maintain the temperature below 10° C
3. 3
   ExtraktionThe mixture was extracted with ethyl acetate (500 mL)
4. 4
   Filtrationthe organic phase was filtered through a Celite pad, which
5. 5
   Waschenwas washed once with ethyl acetate (150 mL)
6. 6
   WaschenThe combined organics phases were washed with brine
7. 7
   Sonstigedried
8. 8
   Sonstigesolvent was evaporated in vacuo
9. 9
   SonstigeThe resulting solid was recrystallized from toluene

Vorschrift

A solution of 2-(3-nitrophenyl)quinoxaline (9.4 g, 37.4 mmol), SnCl2.H2O (28 g, 13.48 mmol) in CHCl3 (95 mL) was heated to 90° C. for 15 minutes, cooled to room temperature, added to ice water (190 mL), and basified to pH 10 with 50% aqueous NaOH, adding ice as necessary to maintain the temperature below 10° C. The mixture was extracted with ethyl acetate (500 mL), and the organic phase was filtered through a Celite pad, which was washed once with ethyl acetate (150 mL). The combined organics phases were washed with brine and dried, and then solvent was evaporated in vacuo. The resulting solid was recrystallized from toluene to afford (3-quinoxalin-2-ylphenyl)amine (5.6 g, 68% yield). LCMS calculated for C14H11N3 (M+H): 222.26. found 222. 1H-NMR (400 MHz, DMSO-d6) δH: 9.42 (1H, s), 8.11-8.00 (2H, m), 7.94-7.75 (2H, m), 7.55 (1H, s), 7.42 (1H, d, J=7 Hz), 7.22 (1H, m), 6.72 (1H, m), 5.42 (2H, br. s).

Quelle