Water → 8-Hydroxy-5,6,7,8-tetrahydroquinoline

HRID 351151Notes

Reaction equation

HRID 351151 reaction equation
C([O:4][CH:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)(=O)C.C([O-])([O-])=O.[K+].[K+].O>CO>[OH:4][CH:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 122262495,6,7,8-Tetrahydroquinolin-8-yl acetate

Product 1

HCID 118159398-Hydroxy-5,6,7,8-tetrahydroquinolineYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-acetoxy-5,6,7,8-tetrahydroquinoline (99.2 g) in methanol (450 mL) was added K2CO3 (144 g, 1.04 mol) and the mixture was stirred at room temperature overnight. The mixture was poured into water (500 mL) and extracted with CHCl3 (3×500 mL) and the combined organic extracts were dried (Na2SO4), and concentrated to provide 71.6 g of 8-hydroxy-5,6,7,8-tetrahydroquinoline as a brown oil. A purified sample (silica gel, 25:1 CH2Cl2-CH3OH) exhibited the following spectral properties: 1H NMR (CDCl3) δ 1.75–1.89 (m, 2H), 1.96–2.06 (m, 1H), 2.25–2.33 (m, 1H), 2.74–2.90 (m, 2H), 4.23 (br s, 1H, OH), 4.72 (dd, 1H J=7.8, 6.3 Hz), 7.12 (dd, 1H, J=7.5, 4.8 Hz), 7.41 (d, 1H, J=7.5 Hz), 8.41 (d, 1H, J=4.8 Hz); 13C NMR (CDCl3) δ 19.60, 28.84, 31.27, 68.87, 122.74, 132.19, 137.40, 147.06, 158.50. ES-MS m/z 150 (M+H).

Workup

  1. extractionextracted with CHCl3 (3×500 mL)
  2. dry with materialthe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b75a1cd5522d43a4a43e5951b36ca58d
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

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