Phosphorus oxychloride → 3-(6-Chloro-1,6-dihydro-pyridazin-4-yl)-N-methyl-benzamide
Reaktionsgleichung
[CH3:1][NH:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:11]=[N:12][NH:13][C:14](=O)[CH:15]=2)[CH:5]=1.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][CH:14]1[NH:13][N:12]=[CH:11][C:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([NH:2][CH3:1])=[O:17])=[CH:15]1Komponenten
3
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
N-Methyl-3-(6-oxo-1,6-dihydro-pyridazin-4-yl)-benzamide (1 eq, 3.14 mmol, 720 mg) is suspended in POCl3 (10 ml) and the reaction mixture is heated at 110° C. for 2 h. After cooling to room temperature, the solvent is removed in vacuo and then ice water is added. The pH is adjusted to pH8 with portionwise addition of sat. aqueous Na2CO3. The aqueous layer is extracted with EtOAc and the combined organic layers are washed with brine, dried over MgSO4, filtered and evaporated to dryness to yield 3-(6-Chloro-1,6-dihydro-pyridazin-4-yl)-N-methyl-benzamide as a yellow solid which did not require further purification; [M+H]+=248