Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate → 7-Methoxy-3-ethoxycarbonylquinoline hydrochloride

HRID 495477Notes

Reaction equation

HRID 495477 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:18])=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[N:10]2)=[CH:5][CH:4]=1>CCO.[Pd]>[ClH:18].[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 728976Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate

Product 1

HCID 223268747-Methoxy-3-ethoxycarbonylquinoline hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred suspension of 7-methoxy-4-chloro-3-ethoxycarbonylquinoline (Step B, 1.53 g, 5 mmol) in EtOH (15 mL) under inert atmosphere was added Pd/C 10% (153 mg). The mixture was stirred at RT under H2 (atmospheric pressure) for 2 h. The mixture was filtered and solvent removed under vacuum to give crude 7-methoxy-3-ethoxycarbonylquinoline hydrochloride.

Workup

  1. filtrationThe mixture was filtered
  2. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-2b6b7ba4981e4432aba3692216a4cce2
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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