反应详情

温度

100 °C

The suspension of (2E)-2-[bis(methyloxy)methyl]-3-(2,3-dimethylphenyl)-2-propenenitrile (1.55 g, 9.2 mmol) and 10% Pd/C (36 mg, 0.33 mmol) in methanol (25 mL) was hydrogenated using the Parr shaker (23° C., 50 bar) overnight. The catalyst was removed by filtration. Concentration of filtrate gave desire product. (0.26 g, 17%). To a solution of 2-[(2,3-dimethylphenyl)methyl]-3,3-bis(methyloxy)propanenitrile (257 mg, 1.1 mmol) and hydrazine monohydrate (55.1 mg, 1.1 mmol) in ethanol (15 ml) stirred under nitrogen at room temperature was added a solution of 36% HCl (558 mg, 5.51 mmol) dropwise. The reaction mixture was stirred at 100° C. for overnight. Reaction mixture was concentrated and dissolved with ethyl acetate (30 mL) and water (10 mL). pH of aqueous layer was adjusted to 8˜9. Two layers were separated. Organic layer was washed with brine (5 mL), dried and concentrated. Crude product was purified with silica gel column (0-10 methanol/DCM). Product was obtained and used in next step. (191 mg, 86%); LC/MS: MS (ES+) m/e 202 (MH+).

1. customthe Parr shaker (23° C., 50 bar) overnight
2. customThe catalyst was removed by filtration
3. customConcentration of filtrate gave desire product
4. customReaction mixture
5. concentrationwas concentrated
6. dissolutiondissolved with ethyl acetate (30 mL) and water (10 mL)
7. customTwo layers were separated
8. washOrganic layer was washed with brine (5 mL)
9. customdried
10. concentrationconcentrated
11. customCrude product was purified with silica gel column (0-10 methanol/DCM)
12. customProduct was obtained