8-(2-Methoxyethoxy)quinoline → 1,2,3,4-Tetrahydro-8-methoxyethoxyquinoline

HRID 279974Notes

Reaction equation

HRID 279974 reaction equation
[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]2

Participants

4

Reactant 1

HCID 540377188-(2-Methoxyethoxy)quinoline

Product 1

HCID 233230551,2,3,4-Tetrahydro-8-methoxyethoxyquinoline

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  1. customThe catalyst was removed
  2. customThe dark brown oil which remained was purified on a short silica gel column
  3. washethyl acetate for elution

Sources & evidence

ORD record
ord-7a9cd8a51b0e46b084096ed0914052f1
Source dataset
uspto-grants-1986_05
Patent number
US04587341

Reaction notes

Loading…