反应详情

3-Methoxy-3-(4-nitrophenyl)-2-cyanoacrylonitrile (14.4 g, 0.063 mol) was suspended in ethanol (1 L) in a flask equipped with a magnetic stirrer. To the suspension was added 60 mL (ca. 0.20 mol) of a 10% (w/w) solution of ammonia in methanol. The mixture was stirred vigorously for 15 min, at which time HPLC analysis showed the absence of starting material. The now homogeneous mixture was concentrated in vacuo to ca. 80 mL. The solid that had formed was collected with the aid of a small amount of additional ethanol and was pressed well with rubber dam. The cake was washed with of ethanol (2×5 mL) and was left to dry in a hood draft. The dry solid weighed 8.8 g. The filtrate was concentrated and mixed with dichloromethane (10 mL). The resulting solid was collected, washed with dichloromethane (2×2 mL), dried, and combined with the 1st crop to yield 9.9 g (46% for 2 steps). HPLC analysis indicated a purity of 91%. NMR (60 MHz) (DMSO-d6) δ 8.8 (bs, 0.5H); 8.0 (AB, 4H); 3.2 (bs, 1H); 2.8 (bs, 0.5H). The IR spectrum showed nitrile stretches at 2221 and 2207 cm−1.

1. customequipped with a magnetic stirrer
2. concentrationThe now homogeneous mixture was concentrated in vacuo to ca. 80 mL
3. customThe solid that had formed
4. customwas collected with the aid of a small amount of additional ethanol
5. washThe cake was washed with of ethanol (2×5 mL)
6. waitwas left
7. customto dry in a hood draft
8. concentrationThe filtrate was concentrated
9. additionmixed with dichloromethane (10 mL)
10. customThe resulting solid was collected
11. washwashed with dichloromethane (2×2 mL)
12. customdried
13. customto yield 9.9 g (46% for 2 steps)