Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate → Ethyl 7-methoxyquinoline-3-carboxylate

HRID 454186Notes

Reaction equation

HRID 454186 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)(=O)C.[Pd]>[CH2:17]([O:16][C:14]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:2]=1)=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)=[O:15])[CH3:18]

Participants

4

Reactant 1

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

Product 1

HCID 21865246Ethyl 7-methoxyquinoline-3-carboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

4-Chloro-3-ethoxycarbonyl-7-methoxyquinoline (43 g, 162 mmol) was dissolved in acetic acid (250 ml), with 10% palladium on charcoal (1.5 g) and hydrogenated at atmospheric pressure during 8 hours. The catalyst was removed by filtration over a pad of celite and the solvent evaporated. The residue was diluted with water and the pH adjusted to 7-8 with a saturated solution of sodium hydrogen carbonate. The solid was collected by filtration, washed with water and dried under vacuum over phosphorus pentoxide to give 3-ethoxycarbonyl-7-methoxyquinoline (33g, 88%) as a beige powder.

Workup

  1. customThe catalyst was removed by filtration over a pad of celite
  2. customthe solvent evaporated
  3. additionThe residue was diluted with water
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. dry with materialdried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-5c4c656eb0f64dd78cc7cab723e9172f
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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