Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate → Ethyl 6-methoxyquinoline-3-carboxylate

HRID 1640117Notes

Reaction equation

HRID 1640117 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CO.[Pd]>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:2]2

Participants

4

Reactant 1

HCID 304558Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate

Product 1

HCID 304668Ethyl 6-methoxyquinoline-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate (640 mg, 2.4 mmol) was dissolved in MeOH (30 mL). TEA (0.67 mL, 4.8 mmol) and 10% Pd on carbon (0.1 g) were added. The mixture was allowed to stir under an atmosphere of hydrogen (50 psi) for 20 h and was then filtered through Celite. Removal of solvents gave ethyl 6-methoxyquinoline-3-carboxylate, which was used without further purification. LCMS: (FA) ES+ 232.0.

Workup

  1. filtrationwas then filtered through Celite
  2. customRemoval of solvents

Sources & evidence

ORD record
ord-30c9a28d8f834676ae1127ce64eece43
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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