反应详情

A mixture of 4,4-dimethyl-3-oxo-pentanenitrile (4.52 g, 36.15 mmol), 4-hydrazinobenzoic acid (5.00 g, 32.86 mmol), and acetic acid (2 mL) in EtOH/THF (1:1) was refluxed for 16 h. After cooling, the solvent was concentrated at reduced pressure, and the crude was re-dissolved in EtOAc. The organic layer was washed with aqueous saturated Na2CO3 solution and brine, dried over MgSO4, filtered, and concentrated to half its volume. The resulting residue was filtered, and the solids were washed with cold EtOAc and dried under high vacuum to afford the title compound as a white solid (8.4 g, 99%). 1H-NMR (DMSO-d6) δ 12.91 (s, 1H), 7.99 (d, J=6.0 Hz, 2H), 7.75 (d, J=9.0 Hz, 2H), 5.42 (s, 1H), 5.39 (s, 2H), 1.21 (s, 9H); MS LC-MS [M+H]+=260, RT=1.83 min.

1. temperaturewas refluxed for 16 h
2. temperatureAfter cooling
3. concentrationthe solvent was concentrated at reduced pressure
4. dissolutionthe crude was re-dissolved in EtOAc
5. washThe organic layer was washed with aqueous saturated Na2CO3 solution and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated to half its volume
9. filtrationThe resulting residue was filtered
10. washthe solids were washed with cold EtOAc
11. customdried under high vacuum