反应详情

In a 50-mL egg-plant flask, 1.0 ml of water, 0.99 g (9.5 mmole) of 3-cyanopyridine and 5.5 g (0.095 mole) of a hydrazine monohydrate were charged and they were reacted at 30° C. for 3 hours under stirring. After disappearance of raw materials was confirmed by HPLC analysis, 10 ml of toluene was added and from the resulting mixture, water and excess hydrazine were distilled off under reduced pressure. This operation was repeated three times in total. To the residue were added 5.5 ml of water and 5.5 ml of ethanol, followed by the addition of 2.0 g (9.5 mmole) of Benzil. The mixture was reacted for 2 hours at an external temperature of 100° C. To the reaction mixture was added 10 ml of toluene and the solvent was distilled off under reduced pressure. In 10 ml of xylene, 8.8 g (0.095 mole) of 2,5-norbornadiene was dissolved. The resulting solution was added to the residue, followed by reaction for 24 hours under reflux. After completion of the reaction, xylene and excess 2,5-norbornadiene were distilled off under reduced pressure. To the residue was added 10 ml of toluene and 2,5-norbornadiene was completely distilled off. The residue was purified by chromatography on a silica gel column, followed by recrystallization from hexane, whereby 1.8 g (yield: 63.2%) of the target compound was obtained as pale yellow crystals. The product was found to have a purity of 99.3%.

1. customthey were reacted at 30° C. for 3 hours
2. distillationwere distilled off under reduced pressure
3. additionTo the residue were added 5.5 ml of water and 5.5 ml of ethanol
4. customThe mixture was reacted for 2 hours at an external temperature of 100° C
5. distillationthe solvent was distilled off under reduced pressure
6. additionThe resulting solution was added to the residue
7. customfollowed by reaction for 24 hours
8. temperatureunder reflux
9. distillationwere distilled off under reduced pressure
10. additionTo the residue was added 10 ml of toluene and 2,5-norbornadiene
11. distillationwas completely distilled off
12. customThe residue was purified by chromatography on a silica gel column
13. customfollowed by recrystallization from hexane