Nitrogen → Ethyl 6-methoxyquinoline-3-carboxylate

HRID 2115792Notes

Reaction equation

HRID 2115792 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].N#N>CCO.C(Cl)Cl.[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

6

Reactant 2

HCID 947NitrogenHCID 304558Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate

Product 1

HCID 304668Ethyl 6-methoxyquinoline-3-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-chloro-6-methoxyquinoline-3-carboxylate (Step b, 18 g, 68 mmol) in EtOH (200 mL) stirred under N2 was introduced Pd/C 10% (2 g). The N2 atmosphere was replaced by H2 and the mixture was vigourously stirred at RT under H2 atmosphere (balloon) overnight. The mixture was diluted with DCM and filtered. The catalyst was washed several times with DCM. The solvents were removed under vacuum. The solid residue was suspended in EtOH and the filtered to give ethyl 6-methoxyquinoline-3-carboxylate.

Workup

  1. filtrationfiltered
  2. washThe catalyst was washed several times with DCM
  3. customThe solvents were removed under vacuum
  4. filtrationthe filtered

Sources & evidence

ORD record
ord-585d6b479f254e1aae03f73cc1d7c6b3
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

Loading…