反应详情

温度

90 °C

To a solution of 5.8 g (16.2 mmol) 2-1 in 100 mL of pyridine was added 1.18 mL (24.3 mmol) hydrazine hydrate. The reaction was heated at 90° C. for 45 minutes, cooled to room temperature, and then to 0° C. Following the addition of 5.75 mL (80.9 mmol) of acetyl chloride, the cooling bath was removed and the reaction was stirred for 7 h. The reaction was dumped into a separatory funnel with EtOAc and brine. The layers were separated, the organic phase was washed twice with 1M HCl, brine, dried over Na2SO4, and concentrated. The residue was twice dissolved in toluene and again concentrated to remove any remaining pyridine. The residue was dissolved in 100 mL of MeOH, 1.5 g (7.9 mmol) of p-toluenesulphonic acid was added, and the mixture was stirred for 2 h at room temperature. The reaction was concentrated, the residue was dissolved in EtOAc, washed twice with a saturated solution of NaHCO3, brine, dried over Na2CO3, and concentrated. The residue was triturated with Et2O and filtered to provide 2-2 as a white solid. Data for 2-2: LC-MS: rt=2.20 min, m/z=331 (M+1).

1. temperaturecooled to room temperature
2. customto 0° C
3. customthe cooling bath was removed
4. customThe reaction was dumped into a separatory funnel with EtOAc and brine
5. customThe layers were separated
6. washthe organic phase was washed twice with 1M HCl, brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. dissolutionThe residue was twice dissolved in toluene
10. concentrationagain concentrated
11. customto remove any remaining pyridine
12. dissolutionThe residue was dissolved in 100 mL of MeOH
13. stirringthe mixture was stirred for 2 h at room temperature
14. concentrationThe reaction was concentrated
15. dissolutionthe residue was dissolved in EtOAc
16. washwashed twice with a saturated solution of NaHCO3, brine
17. dry with materialdried over Na2CO3
18. concentrationconcentrated
19. customThe residue was triturated with Et2O
20. filtrationfiltered