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

HRID 1680536Notes

Reaction equation

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]

Participants

Conditions

Temperature: 110 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-e505b4261c8042528c51e43653403644
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04273932

Reaction notes

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