Dimethylformamide → 2-Tert-butyl-5-dimethylamino-4-formyl-3(2H)-pyridazinone

Reaction equation

P(Cl)(Cl)(Cl)=O.[C:6]([N:10]1[C:15](=[O:16])[CH:14]=[C:13]([N:17]([CH3:19])[CH3:18])[CH:12]=[N:11]1)([CH3:9])([CH3:8])[CH3:7].CN([CH:23]=[O:24])C>>[C:6]([N:10]1[C:15](=[O:16])[C:14]([CH:23]=[O:24])=[C:13]([N:17]([CH3:19])[CH3:18])[CH:12]=[N:11]1)([CH3:9])([CH3:8])[CH3:7]

Participants

Reactant 3

HCID 6228Dimethylformamide2×

HCID 24813Phosphorus oxychloride

HCID 189189072-t-butyl-5-dimethylamino-3(2H)-pyridazinone

Product 1

HCID 189188952-Tert-butyl-5-dimethylamino-4-formyl-3(2H)-pyridazinone

Procedure

Phosphorus oxychloride (6.5 g) was added dropwise to DMF (15 ml) with ice-cooling and the mixture was stirred at room temperature for 30 minutes. Then, 2-t-butyl-5-dimethylamino-3(2H)-pyridazinone (3.3 g)/DMF (40 ml) was added dropwise with ice-cooling and the mixture was stirred at 70° C. for 1 hour. This reaction mixture was poured gradually into ice-NaHCO3 /water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated to dryness. The residue was washed with n-hexane and dried. Yellow powder, 3.7 g. 1H-NMR (CDCl3) δ: 1.63(9H,s), 3.10(6H,s), 7.71(1H,s), 10.27(1H,s).