Triethylamine → HCID 58959712, compound

HRID 915788Notes

Reaction equation

HRID 915788 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:7](=[O:21])[CH:8]=[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:10][C:11]=2[C:12](Cl)=[CH:13][CH:14]=1)=[O:4].CCN(CC)CC>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:7](=[O:21])[CH:8]=[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:4]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 589596858-Chloro-4-oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid 2-ethyl 5-methyl ester

Product 1

HCID 58959712HCID 58959712, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 24 (4.50 g, 14.5 mmol) in EtOAc (100 mL) was added Et3N (50 mL). The reaction mixture was heated to 50° C. to generate a clear solution. 10% Pd/C (0.500 g) was added carefully. The reaction mixture was hydrogenated (50 psi) on a Parr hydrogenation apparatus at room temperature for 4 h. Then the catalyst was filtered off on a pad of celite and the filtrate washed with water (100 mL). The aqueous layer was extracted with EtOAc (100 mL) and the combined organic layers were dried (MgSO4), filtered, and concentrated. The crude residue was washed with Et2O (100 mL) to give an off-white solid (29, 3.46 g, 99.1%). 1H NMR (DMSO-d6, 300 MHz) δ ?8.05 (d, J=8.6 Hz, 1H), 7.75 (t, J=8.6 Hz, 1H), 7.29 (d, J=8.6 Hz, 1H), 6.63 (s, 1H), 4.44 (q, J=7.3 Hz, 2H), 3.80 (s, 3H), 1.37 (t, J=7.3 Hz, 3H).

Workup

  1. customat room temperature
  2. customfor 4 h
  3. filtrationThen the catalyst was filtered off on a pad of celite
  4. washthe filtrate washed with water (100 mL)
  5. extractionThe aqueous layer was extracted with EtOAc (100 mL)
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washThe crude residue was washed with Et2O (100 mL)
  10. customto give an off-white solid (29, 3.46 g, 99.1%)

Sources & evidence

ORD record
ord-6271b144e7a240ffbdfebce181c38ba0
Source dataset
uspto-grants-2007_09
Patent number
US07268138B2

Reaction notes

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