1,1-Dimethoxyethyl(dimethyl)amine → 3-(3-Methyl-1,2,4-oxadiazol-5-yl)benzaldehyde
Reaction equation
O1CC[O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([NH2:11])=[O:10].CO[C:17](OC)([N:19](C)C)[CH3:18]>>[CH3:18][C:17]1[N:11]=[C:9]([C:8]2[CH:7]=[C:6]([CH:14]=[CH:13][CH:12]=2)[CH:2]=[O:3])[O:10][N:19]=1Participants
3
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 3-[1,3]dioxolan-2-yl-benzamide (2.3 g) and dimethylacetamide dimethylacetal (4 g) was heated under reflux for 1 hour and then evaporated to dryness. The oily residue was dissolved in dioxane (20 mL) and hydroxylamine hydrochloride (1.18 g), acetic acid (20 mL) and a 2N aqueous sodium hydroxide solution (9 mL) were added and the mixture was heated at 90° C. for 2 hours. After evaporation, the residue was dissolved in toluene (100 mL) and a 1N hydrochloric acid solution (50 mL) was added and the mixture was stirred at reflux for 2 hours. After cooling at room temperature the organic phase was decanted, washed with water, dried over Na2SO4, filtered and evaporated to give the title compound (2.3 g) as a white solid.