Reaktion #519887

Reaktionsgleichung

5-methyl-6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline

triphenylphosphine

sodium hydroxide water

→

2-methyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinoline-4-amine

Ausbeute 23.4%

Lösungsmittel

ether

1,2-dichlorobenzene

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturat reflux for 18 hours
3. 3
   Sonstigethe solvent was removed in vacuo
4. 4
   workup.ADDITIONThe resulting residue was treated with 1N HCl/water (30 ml)
5. 5
   Sonstigeproduced an off white suspension
6. 6
   SonstigeThe solid was removed by filtration
7. 7
   Sonstigeleaving a yellow filtrate
8. 8
   ExtraktionThe filtrate was extracted with dichloromethane (3×25 ml)
9. 9
   WaschenThe combined organic fractions were washed with brine (25 ml)
10. 10
    Trocknendried (Na2SO4)
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated in vaeuo
13. 13
    Sonstigeto yield an orange oil
14. 14
    Sonstigeto produce a precipitate
15. 15
    SonstigeThe solid was recrystallized from n-propyl acetate

Vorschrift

Under an atmosphere of nitrogen, 5-methyl-6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline (0.73 g, 1.89 mmol) and triphenylphosphine (0.64 g, 2.84 mmol) were dissolved in 1,2-dichlorobenzene (15 ml). The reaction was heated at reflux for 18 hours. After cooling to ambient temperature, the solvent was removed in vacuo. The resulting residue was treated with 1N HCl/water (30 ml) and vigorous stirring produced an off white suspension. The solid was removed by filtration leaving a yellow filtrate. The filtrate was treated with 10% sodium hydroxide/water until pH 11 was reached. The filtrate was extracted with dichloromethane (3×25 ml). The combined organic fractions were washed with brine (25 ml), dried (Na2SO4), filtered and concentrated in vaeuo to yield an orange oil. The oil was dissolved in a minimum amount of dichloromethane and diluted with ether to produce a precipitate. The solid was recrystallized from n-propyl acetate to yield 0.16 g of 2-methyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinoline-4-amine as a tan solid, m.p. 145.0-146.0.

Quelle