HCID 90417413, compound → HCID 136629534, compound

HRID 1748375Notes

Reaction equation

HRID 1748375 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[N:10]2)=[CH:5][CH:4]=1.ClC1C(CC(OCC)=O)=CC2C(=CC(OC)=CC=2)N=1.ClC1C(CC(OCC)=O)=CC2C(=CC=CC=2OC)N=1>CCOC(C)=O.CCO.[Pd]>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 90417413HCID 90417413, compoundHCID 90417428HCID 90417428, compoundHCID 90417558HCID 90417558, compound

Product 1

HCID 136629534HCID 136629534, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-(7-methoxyquinolin-3-yl)acetate. To a solution of a crude mixture of ethyl 2-(2-chloro-7-methoxyquinolin-3-yl)acetate and ethyl 2-(2-chloro-5-methoxyquinolin-3-yl)acetate in EtOAc (200 mL) and EtOH (200 mL) was added 10% Pd/C (50 mg, 0.47 mmol). The reaction mixture was placed under an atmosphere of hydrogen and stirred at ambient temperature for 3 days. The crude reaction mixture was filtered through silica and concentrated to afford a brown oil. Purification by FCC (SiO2, 0-5%, MeOH/DCM) yielded the title compound as a light brown solid (6.0 g, 35% over 2 steps). 1H NMR (400 MHz, CDCl3) δ 8.76 (d, J=2.0 Hz, 1H), 8.00 (d, J=2.3 Hz, 1H), 7.67 (d, J=8.6 Hz, 1H), 7.41 (d, J=2.3 Hz, 1H), 7.20 (dd, J=9.0, 2.3 Hz, 1H), 4.18 (q, J=7.2 Hz, 2H), 3.95 (s, 3H), 3.76 (s, 2H), 1.26 (t, J=6.8 Hz, 3H). [M+H]=246.2.

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered through silica
  3. concentrationconcentrated
  4. customto afford a brown oil
  5. customPurification by FCC (SiO2, 0-5%, MeOH/DCM)

Sources & evidence

ORD record
ord-898dfd2ed44848e69dc8b540c2e8cabc
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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