1,1-Bis(propan-2-yl) 3,3-dimethoxycyclobutane-1,1-dicarboxylate → 7-Chloro-2-phenyl4-trifluoromethyl-quinoline

HRID 244226

反応式

HRID 244226 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:6][CH:7]=1.C(OC(C1(C(OC(C)C)=O)CC(OC)(OC)C1)=O)(C)C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:8]2)=[CH:6][CH:7]=1

参加物

3

反応物 2

HCID 49133591,1-Bis(propan-2-yl) 3,3-dimethoxycyclobutane-1,1-dicarboxylateHCID 666768124-(3-Chloro-phenylamino)-1,1,1-trifluoro-4-phenyl-but-3-en-2-one

生成物 1

HCID 146176127-Chloro-2-phenyl4-trifluoromethyl-quinoline

実験手順

4-(3-Chloro-phenylamino)-1,1,1-trifluoro-4-phenyl-but-3-en-2-one (2.8 g, 0.0086 mole) and polyphosphoric acid (60 mL) in a 250 mL 3 neck round bottom flask was stirred mechanically under an atmosphere of Nitrogen at 165° C. internal temperature for 3 h. The reaction was poured over stirring ice water (600 ml). The product precipitated, and was collected by suction filtration, washed with water, and air dried overnight. The solids remaining in the Buchner funnel, and beaker from aqueous quench were rinsed into a flask concentrated in vacuo, then combined with the filtered sample and chromatographed on silica gel with 3:1 Hexanes/methylene chloride to afford the title compound as a white solid; 1H NMR (CDCl3, 400 MHz) δ 7.53-7.59 (m, 3H), 7.60-7.63 (dd, 1H, J=2.2 & J=9.1 Hz), 8.06-8.09 (dq, 1H, J=1.9 & J=9.0 Hz), 8.16-8.20 (m, 3H), 8.29 (d, 1H, J=2.1 Hz); 19F NMR 8-61.48; MS (ES+): 308.0 (100) [MH+], 310.0 (30) [M+2H+].

後処理

  1. additionThe reaction was poured
  2. customThe product precipitated
  3. filtrationwas collected by suction filtration
  4. washwashed with water, and air
  5. customdried overnight
  6. customfrom aqueous quench
  7. washwere rinsed into a flask
  8. concentrationconcentrated in vacuo
  9. customchromatographed on silica gel with 3:1 Hexanes/methylene chloride

出典と根拠

ORDレコード
ord-4d0f0d6cb98c496d9a81f440ebeb3e10
出典データセット
uspto-grants-2014_02
特許番号
US08653268B2

関連ノート

読み込み中…