Nitrogen → Ethyl 6-methoxyquinoline-3-carboxylate

HRID 1925286Notes

Reaction equation

HRID 1925286 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 vigorously 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-940bf79a6d764d988f6838cba47d18ed
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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