Triethylamine → 4-Oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid 2-ethyl 5-methyl ester

HRID 1091453Notes

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

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

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

Sources & evidence

ORD record: ord-ad366d40f48e4b19ad16bda9331408db
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129382B2

Reaction notes

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