Water → 2-Trifluoromethyl-4-(3-cyanophenyl)-4, 6,7,8-tetrahydro-5(1H)-quinolone

HRID 54461

반응식

HRID 54461 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[NH:12][C:11]([C:20]([F:23])([F:22])[F:21])=[C:10]2C(O)=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].O.C(Cl)Cl.CCOCC.C(OCC)C.CCCCCC>CN1CCCC1=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[NH:12][C:11]([C:20]([F:23])([F:21])[F:22])=[CH:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 101937582-(Trifluoromethyl)-4-(3-cyanophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acidHCID 21584099Diethylether hexaneHCID 21881112Ethyl ether methylene chloride

생성물 1

HCID 111629272-Trifluoromethyl-4-(3-cyanophenyl)-4, 6,7,8-tetrahydro-5(1H)-quinolone수율 99%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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.

후처리

  1. customThe cooled reaction mixture
  2. extractionextracted twice with ethyl ether
  3. washThe combined ether extracts were washed twice with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed
  7. customto yield an off-white solid

출처 및 근거

ORD 기록
ord-d3dae36e4d70465c8f6b72f893e0d140
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622964

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