Hydrochloric Acid → 3-Quinolinecarboxylic acid, 1,2-dihydro-4-hydroxy-1-methyl-2-oxo-, ethyl ester

HRID 346573

Reaktionsgleichung

[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[H][H].[CH3:16][N:17]1C(=O)O[C:20](=[O:21])[C:19]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:18]12.Cl>CC(N(C)C)=O>[CH2:6]([O:5][C:3]([C:2]1[C:1](=[O:9])[N:17]([CH3:16])[C:18]2[C:19]([C:20]=1[OH:21])=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:4])[CH3:7]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A solution of diethyl malonate (8.16 g, 51 mmol) was added slowly to a suspension of sodium hydride (60% in mineral oil, 2.24 g, 56 mmol) in dimethylacetamide under N2 atmosphere. The mixture was stirred at room temperature until the evolution of hydrogen gas ceased, then heated to 90° C. for 30 min. and cooled to room temperature. A solution of N-methylisatoic anhydride (10 g, 56 mmol) in dimethylacetamide was added slowly and the mixture was heated overnight at 120° C. The mixture was then cooled to room temperature, poured into ice water, and acidified by cold 10% HCl. The solids formed were filtered and washed several times by water to yield 8.47 g (67%) of white solids. M.P. 67° C. 1H NMR (DMSO-d6): δ 1.30 (t, J=7.0 Hz, 3H), 3.53 (s, 3H), 4.32 (q, J=7.0 Hz, 2H), 7.30 (t, J=7.5 Hz, 1H), 7.52 (d, J=8.5 Hz, 1H), 7.75 (t, J=8.4 Hz, 1H), 8.04 (d, J=7.8 Hz, 1H), 13.03 (s, 1H). EIMS m/z 248 (M+1), 270 (M+23). Anal. (C13H13NO4) C, H, N.

Aufarbeitung

temperaturecooled to room temperature
temperaturethe mixture was heated overnight at 120° C
temperatureThe mixture was then cooled to room temperature
customThe solids formed
filtrationwere filtered
washwashed several times by water

Quellen und Nachweise

ORD-Eintrag: ord-df011b71f4af45b58eb58875c8f5e0c6
Quelldatensatz: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07173036B2

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