Reaction #7232

Reaction equation

3-methoxyquinoline

TFA

→

3-methoxy-5,6,7,8-tetrahydroquinoline

Yield 87.0%

(3-methoxy-5,6,7,8-tetrahydroquinolin-8-yl)-alcohol

Yield 87.0%

Conditions

Workup

1. 1
   Otherthe suspension bubbled with hydrogen gas 16 h at 60° C
2. 2
   Extractionextracted with CH2Cl2 (3×50 mL)
3. 3
   DryingThe organic extracts were dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   Otherpurified by column chromatography on silica gel (ethyl acetate/hexane; 1:2)

Procedure

To a solution of 3-methoxyquinoline (1.06 g, 6.7 mmol) in TFA (22 mL) under nitrogen was added platinum oxide (225 mg, 1.3 mmol) and the suspension bubbled with hydrogen gas 16 h at 60° C. The mixture was then cooled to room temperature, neutralized to pH 12 with 10 N NaOH and extracted with CH2Cl2 (3×50 mL). The organic extracts were dried (MgSO4), filtered, concentrated and purified by column chromatography on silica gel (ethyl acetate/hexane; 1:2) to give the desired 3-methoxy-5,6,7,8-tetrahydroquinoline (0.95 g, 87%). 1H NMR (CDCl3) δ 1.77 (m, 2H), 1.85 (m, 2H), 2.75 (t, 2H, J=6.0 Hz), 2.85 (t, 2H, J=6.0 Hz), 3.81 (s, 3H), 6.88 (d, 1H, J=1.5 Hz), 8.07 (d, 1H, J=1.5 Hz).

Source