Hydrochloric Acid → 7-Quinolinol, 1,2,3,4-tetrahydro-

HRID 131173Notes

Reaction equation

HRID 131173 reaction equation
C(O)C.Cl.[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[CH:8]=[CH:7][CH:6]=1>O=[Pt]=O.O1CCCC1>[NH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1354268667-Hydroxyquinoline

Product 1

HCID 939807-Quinolinol, 1,2,3,4-tetrahydro-Yield 71%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

PtO2 (528 mg, 2.33 mmol) was added to a dry flask. Ethanol (70 mL), tetrahydrofuran (70 mL), and hydrogen chloride (7.6 mL, 2N) were added after the flask was flushed with argon. Quinolin-7-ol (1000 mg, 6.89 mmol) was added into the flask under argon atmosphere. The solution was degassed and flashed with argon. Hydrogen gas was introduced to the flask by a balloon. The mixture was stirred at H2 atmosphere at room temperature overnight. The mixture was filtered and the filtrate was concentrated. The resulting residue was purified by MPLC (biotage) to afford 730 mg (71%) of the title compound. 1H-NMR (CDCl3) δ 6.77 (d, J=7.6 Hz, 1H), 6.10 (dd, J=8.0 Hz, 2.8 Hz, 1H), 5.95 (d, J=2.4Hz, 1H), 3.24 (t, J=5.9 Hz, 2H), 2.66 (t, J=5.9Hz, 2H), 2.44 (m, 2H); Rf=0.74, 50% ethyl acetate-hexane.

Workup

  1. customwas flushed with argon
  2. customThe solution was degassed
  3. additionHydrogen gas was introduced to the flask by a balloon
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe resulting residue was purified by MPLC (biotage)

Sources & evidence

ORD record
ord-74657ad66fb04642a5768c3a9aa43029
Source dataset
uspto-grants-2008_06
Patent number
US07384947B2

Reaction notes

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