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

HRID 2209544ノート

反応式

HRID 2209544 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-394232c60221424a9679deeacaea0432
出典データセット
uspto-grants-1995_10
特許番号
US05455253

反応ノート

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