Reaktion #542198

Reaktionsgleichung

ether

2-bromo-4′-methylacetophenone

2-amino-5-methyl picoline

K2CO3

→

white solid

Ausbeute 66.1%

6-Methyl-2-(4-methylphenyl)-imidazo[1,2-a]-pyridine

Ausbeute 66.1%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooled to 40° C.
2. 2
   Temperaturcooled by ice-water bath
3. 3
   SonstigeAfter removal of solvent
4. 4
   Filtrationthrough filtration
5. 5
   workup.STIRRINGthe solid was stirred with water (50 ml) for 30 minutes
6. 6
   Filtrationfiltered
7. 7
   Waschenrinsed with water
8. 8
   Sonstigedried under vacuum at 80° C. for 2 hr

Vorschrift

A mixture of 2-bromo-4′-methylacetophenone (90% pure, 10.21 g, 43.11 mmol), 2-amino-5-methyl picoline (4.66 g, 43.11 mmol) and K2CO3 (6.6 g, 47.75 mmol) in absolute EtOH (70 ml) was heated at 93° C. overnight. After cooled to 40° C., ether (100 mL) was added. The mixture was stirred for 30 minutes and cooled by ice-water bath. After removal of solvent through filtration, the solid was stirred with water (50 ml) for 30 minutes and filtered, rinsed with water and dried under vacuum at 80° C. for 2 hr to give 6.33 g of white solid (66.1% yield). m/e+ 223.4 for C15H15N2 (M+H)+; 1H-NMR (400 MHz, CDCl3, δ) 7.84 (m, 3H), 7.71 (d, J=9.531 Hz, 1), 7.51 (d, J=9.165 Hz, 1H), 7.24 (m, 2H), 7.00 (m, 1), 2.38 (s, 3H), 2.29 (d, J=6.23 Hz, 3H) ppm. 13C-NMR (100 MHz, CDCl3 δ) 145.065, 144.444, 137.991, 130.696, 130.635, 129.642, 129.483, 128.391, 128.262, 126.018, 123.652, 122.476, 116.486, 107.857, 21.520, 18.259 ppm.

Quelle