5-Acetamido-4-hydroxy-5,6,7,8-tetrahydroquinoline-3-carboxylic Acid Ethyl Ester → HCID 178474099, Verbindung

HRID 1680536Notizen

Reaktionsgleichung

C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[CH2:10][CH2:11][CH2:12][CH:13]([NH:17][C:18](=[O:20])[CH3:19])[C:14]=2[C:15]=1[OH:16])=[O:5])C>[OH-].[Na+]>[C:18]([NH:17][CH:13]1[CH2:12][CH2:11][CH2:10][C:9]2[N:8]=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[C:15]([OH:16])[C:14]1=2)(=[O:20])[CH3:19]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

5-Acetamido-4-hydroxy-5,6,7,8-tetrahydroquinoline-3-carboxylic acid ethyl ester (0.8 g) was suspended in 20 ml of 1 N sodium hydroxide. The resulting reaction mixture was heated on an oil bath at 110° C. for 2 hours. After being cooled, the reaction mixture was filtered to remove the insoluble matter, and the filtrate was adjusted to pH 2.5 with dilute hydrochloric acid. The precipitate so formed was separated by filtration to obtain a yield of 0.4 g of the desired compound. This compound melted (and decomposed) at 285°-287° C. (uncorrected values). Its infrared absorption spectrum (KBr tablet) had absorption peaks at 3420, 3340, 3260, 3080, 2940, 1710, 1650, 1635, 1290, and 810 cm-1. and its n.m.r. spectrum (CF3COOH, 60Mc, TMS) had signals at δ values of 1.8-2.6 (4H, m), 2.43 (3H, s), 2.9-3.5 (2H, m), 5.72 (1H, d, J=8.3 Hz), 8.47 (1H, d, J=8.3 Hz), and 9.0-9.3 (1H, m).

Aufarbeitung

customThe resulting reaction mixture
temperatureAfter being cooled
filtrationthe reaction mixture was filtered
customto remove the insoluble matter
customThe precipitate so formed
customwas separated by filtration

Quellen und Nachweise

ORD-Eintrag: ord-e505b4261c8042528c51e43653403644
Quelldatensatz: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04273932

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