Trifluoroacetic acid → (3-Methoxy-5,6,7,8-tetrahydroquinolin-8-yl)-alcohol

HRID 7136

Reaction equation

HRID 7136 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.C(O)(C(F)(F)F)=[O:14]>[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[CH:7]([OH:14])[CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 5758073-Methoxyquinoline

Product 1

HCID 22018733(3-Methoxy-5,6,7,8-tetrahydroquinolin-8-yl)-alcoholYield 87%

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

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).

Workup

  1. customthe suspension bubbled with hydrogen gas 16 h at 60° C
  2. extractionextracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography on silica gel (ethyl acetate/hexane; 1:2)

Sources & evidence

ORD record
ord-fe74ddfe194440d1ab2d85f342beb1c2
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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