Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate → HCID 135819170, compound

HRID 1748372Notes

Reaction equation

HRID 1748372 reaction equation
C[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.ClC1C2C(=CC(OC)=CC=2)N=CC=1C(OCC)=O>CCOC(C)=O.C(O)C.[Pd]>[OH: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

6

Reactant 2

HCID 728976Ethyl 4-chloro-7-methoxyquinoline-3-carboxylateHCID 21865246Ethyl 7-methoxyquinoline-3-carboxylate

Product 1

HCID 135819170HCID 135819170, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 7-methoxyquinoline-3-carboxylate. To a solution of ethyl 4-chloro-7-methoxyquinoline-3-carboxylate (1.24 g, 4.67 mmol) in a mixture of EtOAc (30 mL) and ethanol (30 mL) was added 10% Pd/C (10 mg). The flask was evacuated and filled with nitrogen three times and evacuated and filled with hydrogen three times and stirred overnight. After filtration through a plug of silica the reaction mixture was concentrated onto silica. Purification by FCC (SiO2, 0-10% MeOH/DCM) afforded the title compound as a brown solid (955 mg, 89%). 1H NMR (400 MHz, CDCl3) δ 9.37 (d, J=2.0 Hz, 1H), 8.75 (d, J=2.0 Hz, 1H), 7.80 (d, J=9.0 Hz, 1H), 7.47 (d, J=2.3 Hz, 1H), 7.27 (d, J=2.3 Hz, 1H), 4.45 (q, J=7.0 Hz, 2H), 4.01-3.93 (m, 3H), 1.44 (t, J=7.2 Hz, 3H). [M+H]=232.2.

Workup

  1. customThe flask was evacuated
  2. additionfilled with nitrogen three times
  3. customevacuated
  4. additionfilled with hydrogen three times
  5. filtrationAfter filtration through a plug of silica the reaction mixture
  6. concentrationwas concentrated onto silica
  7. customPurification by FCC (SiO2, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-cab321cd62524cb8ba13a7e6ebe007a3
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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