4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

269-270℃

Boiling point:

358℃

Density 

1.429

Flash point:

171℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

0.80±0.20(Predicted)

form 

Solid

color 

Off-White to Light Yellow

λmax

310nm(DMSO)(lit.)

InChI

InChI=1S/C10H7NO3/c12-9-6-3-1-2-4-8(6)11-5-7(9)10(13)14/h1-5H,(H,11,12)(H,13,14)

InChIKey

ILNJBIQQAIIMEY-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2)C(=O)C(C(O)=O)=C1

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HS Code 

2933.99.8290

HazardClass 

IRRITANT

4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID Usage And Synthesis

Uses

4-Oxo-1,4-dihydroquinoline Carboxylic Acid is a novel HIV-1 integrase strand transfer inhibitor.

Synthesis

General procedure for the synthesis of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid from ethyl 4-hydroxyquinoline-3-carboxylate: ethyl 4-hydroxyquinoline-3-carboxylate (15 g, 69 mmol) was suspended in 2N sodium hydroxide solution (150 mL), and the reaction was stirred under refluxing conditions for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered to remove insoluble material. The filtrate was acidified to pH 4 with 2N hydrochloric acid and a white precipitate was precipitated. The precipitate was collected by filtration, washed several times with deionized water and finally dried under vacuum to afford 4-oxo-1,4-dihydroquinoline-3-carboxylic acid as a light white solid (10.5 g, 92% yield). The product was characterized by 1H NMR (DMSO-d6): δ 15.34 (s, 1H), 13.42 (s, 1H), 8.89 (s, 1H), 8.28 (d, J=8.0 Hz, 1H), 7.88 (m, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.60 (m, 1H).

References

[1] Patent: US2008/90864, 2008, A1. Location in patent: Page/Page column 7
[2] Patent: WO2007/79139, 2007, A2. Location in patent: Page/Page column 46; 47
[3] Patent: US2012/309758, 2012, A1. Location in patent: Page/Page column 61
[4] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 0352
[5] Patent: WO2018/64632, 2018, A1. Location in patent: Paragraph 00215; 00216

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