تفاعل #82739

معادلة التفاعل

methylene chloride ether

ethyl ether hexane

water

(-)-4-(3-cyanophenyl)-2-trifluoromethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid

→

title compound

المردود 99.0%

(-)-4-(3-Cyanophenyl)-2-trifluoromethyl-4,6,7,8-tetrahydro-5 (1H)-quinolone

المردود 99.0%

المذيبات

N-methylpyrrolidin-2-one

ظروف التفاعل

المعالجة

1. 1
   أخرىThe cooled reaction mixture
2. 2
   استخلاصextracted twice with ethyl ether
3. 3
   غسيلThe combined ether extracts were washed twice with water
4. 4
   تجفيفdried (MgSO4)
5. 5
   ترشيحfiltered
6. 6
   أخرىthe solvent removed
7. 7
   أخرىto yield an off-white solid

الإجراء التجريبي

A stirred solution of (-)-4-(3-cyanophenyl)-2-trifluoromethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid (3.93 g, 10.85 mmol) in N-methylpyrrolidin-2-one (24 mL) was placed in a preheated oil bath at 210° C. for 20 minutes. The cooled reaction mixture was then poured into water (200 mL) and extracted twice with ethyl ether. The combined ether extracts were washed twice with water, dried (MgSO4), filtered and the solvent removed to yield an off-white solid. Chromatography (eluent: methylene chloride/ether 9:1) and trituration with ethyl ether/hexane provided the title compound (3.42 g, 79%) as a white solid mp 187°-189° C. NMR: 1.88-1.91 (m,2H, CH2), 2.21-2.25 (m,2H, CH2), 2.53-2.64 (m,2H, CH2), 4.68(d,1H, J=5.3 Hz, CH), 5.61 (d,1H, J=5.3 Hz, CH), 7.50-7.54 (m,2H, Ar), 7.61-7.66 (m,2H, Ar), 9.42 (s,1H, NH); MS: m/z=319(M+1); [α]D23 =-606.8° (c=0.665 methanol). Analysis for C17H13F3N2O: Calculated: C, 64.14; H, 4.12; N, 8.80; Found: C, 64.07; H, 4.24; N, 8.78.

المصدر