8-(Benzyloxy)-2-methoxyquinoline → 8-Quinolinol, 2-methoxy-

HRID 1429507Notes

Reaction equation

HRID 1429507 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([O:19][CH3:20])[CH:15]=[CH:14]2)C1C=CC=CC=1>CCO.[Pd]>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]2[C:18](=[C:9]([OH:8])[CH:10]=[CH:11][CH:12]=2)[N:17]=1

Participants

4

Reactant 1

HCID 673664878-(Benzyloxy)-2-methoxyquinoline

Product 1

HCID 7627198-Quinolinol, 2-methoxy-Yield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 8-(benzyloxy)-2-methoxyquinoline (2.2 g, 8.3 mmol) in EtOH (40 mL) was added Pd/C (230 mg). The mixture was stirred at 25° C. for 16 h under an atmosphere of H2. The mixture was filtered, and the filtrate was evaporated to give the desired compound (1.2 g, 83%). 1HNMR (CDCl3, 400 MHz) δ: 7.91 (d, J=8.8 Hz, 1H), 7.52 (br. s., 1H), 7.23-7.15 (m, 2H), 7.07 (dd, J=1.4, 7.2 Hz, 1H), 6.85 (d, J=8.8 Hz, 1H), 3.99 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-72b40427201148dfa339d568f6dc606f
Source dataset
uspto-grants-2015_01
Patent number
US08940726B2

Reaction notes

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