تفاعل #168242

معادلة التفاعل

3-amino-3-(4-phenoxyphenyl)acrylonitrile

methyl 4-(3-methoxy-3-oxopropanoyl)benzoate

ammonium chloride

→

methyl 4-(5-cyano-4-oxo-6-(4-phenoxyphenyl)-1,4-dihydropyridin-2-yl)benzoate

المردود 65.0%

ظروف التفاعل

المعالجة

1. 1
   أخرىwas microwaved at 230° C. for 20 min
2. 2
   استخلاصextracted with ethyl acetate (80 mL)
3. 3
   غسيلThe ethyl acetate phase was washed with saturated ammonium chloride (10 mL), water (10 mL), brine (5 mL)
4. 4
   تجفيفdried (MgSO4)
5. 5
   تركيزconcentrated
6. 6
   غسيلSilica gel chromatography, eluting with 0-80% ethyl acetate in hexanes
7. 7
   أخرىgave impure products
8. 8
   أخرىThe material was triturated with dichloromethane
9. 9
   ترشيحThe white solid was collected by filtration

الإجراء التجريبي

A mixture of 3-amino-3-(4-phenoxyphenyl)acrylonitrile (0.517 g, 2.188 mmol) and methyl 4-(3-methoxy-3-oxopropanoyl)benzoate (2.068 g, 8.75 mmol) was microwaved at 230° C. for 20 min. After cooling to room temperature, the mixture was poured into saturated ammonium chloride (25 mL) and extracted with ethyl acetate (80 mL). The ethyl acetate phase was washed with saturated ammonium chloride (10 mL), water (10 mL), brine (5 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 0-80% ethyl acetate in hexanes, gave impure products. The material was triturated with dichloromethane. The white solid was collected by filtration to give methyl 4-(5-cyano-4-oxo-6-(4-phenoxyphenyl)-1,4-dihydropyridin-2-yl)benzoate (0.598 g, 65% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.25 (1H, br. s), 8.17 (2H, br. s), 8.02 (1H, br. s), 7.71 (2H, br. s), 7.40 (2H, t, J=7.91 Hz), 7.24 (1H, br. s), 7.03-7.16 (4H, m), 6.62 (1H, br. s), 3.95 (3H, s); MS (ES+) m/z: 423 (M−H); LC retention time: 4.118 min (analytical HPLC Method A).

المصدر