反应详情

温度

80 °C

Hydrazine hydrochloride (0.14 g, 2 mmol) is added to 4-[(2Z)-2-(dimethylaminomethylene)-4,4-dimethyl-3-oxo-cyclohexyl]-3-methyl-benzonitrile (0.2 g, 0.67 mmol) in ethanol (30 mL), then acetic acid (two drops) is added to the mixture. After the addition is complete, the reaction mixture is stirred at 80° C. for 3 h. The mixture is cooled to room temperature and concentrated in vacuo. The residue is diluted with ethyl acetate (50 mL) and saturated sodium bicarbonate solution (50 mL). The organic phase is separated and the aqueous phase extracted with ethyl acetate (3×50 mL). The combined organic phase is washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (eluted with pet ether:EtOAc=2:1 to 1:1) to give the title compound. The product is added to HCl/ethyl acetate and concentrated in vacuo to give the HCl salt of the title compound (0.12 g, 67%). ES/MS 266 (M+H).

1. additionAfter the addition
2. temperatureThe mixture is cooled to room temperature
3. concentrationconcentrated in vacuo
4. additionThe residue is diluted with ethyl acetate (50 mL) and saturated sodium bicarbonate solution (50 mL)
5. customThe organic phase is separated
6. extractionthe aqueous phase extracted with ethyl acetate (3×50 mL)
7. washThe combined organic phase is washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated in vacuo
10. customThe residue is purified by silica gel column chromatography (eluted with pet ether:EtOAc=2:1 to 1:1)