Reaktion #1951079

Reaktionsgleichung

2-(2,6-dichloro-phenylamino)-1,6,7-trimethyl-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one

selenium dioxide

→

2-(2,6-dichloro-phenylamino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinoline-7-carbaldehyde

Ausbeute 72.4%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 200 mL round bottom flask equipped with a stir bar
2. 2
   SonstigeThe flask was fitted with a condenser
3. 3
   Temperaturheated
4. 4
   Temperaturto reflux for 4.5 h
5. 5
   SonstigeThe reaction was then removed
6. 6
   Temperaturfrom heat
7. 7
   FiltrationThe slightly opaque solution was filtered through celite
8. 8
   Waschenwashed with dichloromethane:methanol (9:1)
9. 9
   EinengenThe solution was concentrated
10. 10
    Sonstigethe resulting residue triturated with dichloromethane

Vorschrift

To a 200 mL round bottom flask equipped with a stir bar was added 2-(2,6-dichloro-phenylamino)-1,6,7-trimethyl-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one (2.4 g, 6.2 mmol), selenium dioxide (2.0 g, 18 mmol) and dioxane (150 mL). The flask was fitted with a condenser and heated to reflux for 4.5 h. The reaction was then removed from heat and allowed to cool to room temperature. The slightly opaque solution was filtered through celite and washed with dichloromethane:methanol (9:1). The solution was concentrated and the resulting residue triturated with dichloromethane to produce 2-(2,6-dichloro-phenylamino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinoline-7-carbaldehyde (1.8 g, 72%) as a brownish yellow solid, which was used without further purification. 1H NMR (400 MHz, DMSO-d6+TFA) δ 10.65 (s, 1H), 10.24 (s, 1H), 7.96 (d, 1H, J=8.6 Hz), 7.78 (d, 1H, J=8.6 Hz), 7.70 (d, 2H, J=7.8 Hz), 7.49 (d, 2H, J=7.8 Hz), 4.15 (s, 3H), 2.70 (s, 3H); ESMS (m/z): found, 401.

Quelle