Reaktion #640171

Reaktionsgleichung

Phosphorous oxychloride

dimethylaniline

6-methoxy-4-hydroxycinnoline

→

6-methoxy-4-chlorocinnoline

Ausbeute 59.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturat reflux for 15 min
3. 3
   Temperaturcooled
4. 4
   Einengenconcentrated under vacuum
5. 5
   SonstigeThe residue was partitioned between chloroform (100 ml) and water (30 ml)
6. 6
   Waschenthe organic layer was washed with brine
7. 7
   Trocknendried (Na2SO4)

Vorschrift

Phosphorous oxychloride (5 ml) was added to a mix of dimethylaniline (157 mg, 1.3 mmol) and 6-methoxy-4-hydroxycinnoline (208 mg, 1.2 mmol). The reaction was heated at reflux for 15 min, then cooled and concentrated under vacuum. The residue was partitioned between chloroform (100 ml) and water (30 ml), then the organic layer was washed with brine and dried (Na2SO4). Chromatography of the residue adsorbed onto silica gel (3 g) on silica gel (15 g) eluent CH2Cl2 to 10% Ethylacetate/CH2Cl2 gave 6-methoxy-4-chlorocinnoline (135 mg, 0.7 mmol) in 59% yield as white yellow solid. δH (CDCl3)=4.03 (s, 3H); 7.28 (d, 1H); 7.51 (dd, 1H); 8.41 (d, 1H) and 9.22 (br s, 1H). MS (ESI) (M+H)+ 195.

Quelle