Quinoline → 1-Azatricyclo[6.3.1.0,4,12]dodeca-2,4,6,8(12)-tetraene

HRID 63550

反応式

HRID 63550 の反応式
[C:1]1(C(O)=O)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.N1C2C(=CC=CC=2)C=CC=1>ClCCl.[Cr]([O-])([O-])=O.[Cu+2]>[CH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1

参加物

5

反応物 2

HCID 7047QuinolineHCID 225568865,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid

生成物 1

HCID 156456291-Azatricyclo[6.3.1.0,4,12]dodeca-2,4,6,8(12)-tetraene収率 72%

試薬・触媒・溶媒 2

HCID 178505374HCID 178505374、化合物触媒HCID 6344Dichloromethane溶媒

反応条件

温度
185 °C

実験手順

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid (37.5 g, 0.186 mol), copper chromite (13.5 g, 43 mmol) and quinoline (180 ml) were heated with stirring to 185° C. for 2 hours. The mixture was cooled, diluted with dichloromethane (1 L) and filtered over hyflo. The filtrate was washed with 2 M hydrochloric acid (2×600 ml) and twice with 2 M sodium hydroxide (150 ml) before being evaporated to dryness. The residue was purified by silica gel chromatography, eluting with a ethyl acetate/hexanes (1:6) to afford 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline (21 g, 72%) as a pale yellow solid. 1H NMR (CDCl3) 400 MHz δ: 7.44 (dd, 1H, J=0.8 and 7.6 Hz), 7.07 (d, 1H, J=3.2 Hz), 7.01 (t, 1H, J=7.2 Hz), 6.9 (dd, 1H, J=0.8 and 6.8 Hz), 6.43 (d, 1H, J=3.2 Hz), 4.16 (t, 2H, J=6 Hz), 2.99 (t, 2H, J=6.4 Hz), 2.24 (m, 2H).

後処理

  1. temperatureThe mixture was cooled
  2. filtrationfiltered over hyflo
  3. washThe filtrate was washed with 2 M hydrochloric acid (2×600 ml) and twice with 2 M sodium hydroxide (150 ml)
  4. custombefore being evaporated to dryness
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with a ethyl acetate/hexanes (1:6)

出典と根拠

ORDレコード
ord-50462e14ce48437783cd65fbc7b83bf6
出典データセット
uspto-grants-2016_09
特許番号
US09447088B2

関連ノート

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