8-(2-Methoxyethoxy)quinoline → 1,2,3,4-Tetrahydro-8-methoxyethoxyquinoline
Reaktionsgleichung
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[CH:11]2>CO.O=[Pt]=O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[NH:14][CH2:13][CH2:12][CH2:11]2Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
8-Methoxyethoxyquinoline (6.48 g, 31.9 mmol) was dissolved in methanol (50 ml) and reduced on a Parr hydrogenation apparatus using PtO2 catalyst. The catalyst was removed, and the solution was taken to dryness. The dark brown oil which remained was purified on a short silica gel column using 4:1 heptane:ethyl acetate for elution. The isolated oil (1,2,3,4-tetrahydro-8-methoxyethoxyquinoline) had the following NMR spectrum: (CDCl3) δ 1.93 (quintet, 2, CH2 (beta-H)), 2.76 (tr, 2, CH2), 3.32 (tr, 2, CH2), 3.43 (s, 3, OMe), 3.72 (tr, 2, OCH2), 4.11 (tr, 2, CH2O), 4.31 (br, 1, NH), 6.57 (s, +sh, 3, Ar-3H). Anal. Calcd. for C12H17NO2 : C, 69.54; H, 8.27; N, 6.76. Found: C, 69.42; H, 8.26; N, 6.70.