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

HRID 856957Notes

Reaction equation

HRID 856957 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=2.4 Hz, 1H), 3.24 (t, J=5.9 Hz, 2H), 2.66 (t, J=5.9 Hz, 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-36bde54ca87b4cc8bcb4de7163ac9667
Source dataset
uspto-grants-2006_12
Patent number
US07144885B2

Reaction notes

Loading…