| Identification | Back Directory | [Name]
4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID | [CAS]
13721-01-2 | [Synonyms]
13721-01-2
AURORA 17733
TIMTEC-BB SBB000272
VX770-INTERMEDIATES
4-Quinolone-3-carboxylic acid
4-Quinolone-3-carboxylic acid-D4
4-Oxo-1,4-dihydroquinoline-3-carboxylicaci
4-Oxo-1,4-dihydroquinoline Carboxylic Acid
4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
1,4-Dihydro-4-oxo-3-quinolinecarboxylic acid
4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID
1,4-DIHYDRO-4-OXO-QUINOLINE-3-CARBOXYLIC ACID
1,2-Dihydro-4-oxo-quinoline-3-carboxylic acid
3-Quinolinecarboxylic acid, 1,4-dihydro-4-oxo-
1,4-Dihydro-4-oxoquinoline-3-carboxylicAcid>
1,4-DIHYDRO-4-OXO-QUINOLINE-3-Carboxylic Acid (CAS-13721-01-2)
4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID ISO 9001：2015 REACH | [Molecular Formula]
C10H7NO3 | [MDL Number]
MFCD00498984 | [MOL File]
13721-01-2.mol | [Molecular Weight]
189.17 |
| Chemical Properties | Back Directory | [Melting point ]
269-270℃ | [Boiling point ]
358℃ | [density ]
1.429 | [Fp ]
171℃ | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
0.80±0.20(Predicted) | [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 |
| Hazard Information | Back Directory | [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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