1-(Quinolin-2-yl)ethan-1-one → 2-(1-Hydroxyethyl)tetrahydroquinoline

HRID 52544Notes

Reaction equation

HRID 52544 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)(=[O:3])[CH3:2].[H][H]>C(O)(=O)C.[Pt]=O>[OH:3][CH:1]([CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1)[CH3:2]

Participants

5

Reactant 2

HCID 3187031-(Quinolin-2-yl)ethan-1-oneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 199632352-(1-Hydroxyethyl)tetrahydroquinolineYield 78%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

2-Acetylquinoline (21.0 g, 0.123 mol) in acetic acid (210 mL) was hydrogenated over platinum oxide (1.0 g) under atmospheric pressure of hydrogen at room temperature until the theoretical amount of hydrogen was consumed. The mixture was passed through celite and concentrated. The residue was purified by column chromatography with 5:1 to 1:1 hexane/ethyl acetate to give 16.85 g of 2-(1-hydroxyethyl)tetrahydroquinoline (78%): 1H NMR (270 MHz, CDCl3) δ6.95 (m, 2H), 6.62 (td, 1H, J=7.3, 1 Hz), 6.51 (dd, 1H, J=7.3, 1 Hz), 3.81 (dq, 1H, J=10.2, 6.6 Hz), 1.87 (m, 1H), 1.76 (m, 1H), 1.20 (d, 3H, J=6.6 Hz).

Workup

  1. customwas consumed
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography with 5:1 to 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-c72f19833a7b4c878e2ad89cda005bda
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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