| Identification | More | [Name]
2-CHLOROQUINOLINE-4-CARBOXYLIC ACID | [CAS]
5467-57-2 | [Synonyms]
2-CHLORO-4-CARBOXY QUINOLINE
2-CHLOROQUINOLINE-4-CARBOXYLIC ACID
A-CHLORO CINCHONINIC ACID
AKOS BB-6908
2-chloroquinazoline-4-carboxylic acid ethyl ester | [Molecular Formula]
C10H6ClNO2 | [MDL Number]
MFCD00023940 | [Molecular Weight]
207.61 | [MOL File]
5467-57-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
244 °C | [Boiling point ]
368.7±22.0 °C(Predicted) | [density ]
1.469±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
2.17±0.10(Predicted) | [color ]
White to Orange to Green | [InChI]
InChI=1S/C10H6ClNO2/c11-9-5-7(10(13)14)6-3-1-2-4-8(6)12-9/h1-5H,(H,13,14) | [InChIKey]
ICNCOMYUODLTAI-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC=CC=2)C(C(O)=O)=CC=1Cl | [CAS DataBase Reference]
5467-57-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [HazardClass ]
IRRITANT | [HS Code ]
2933491090 |
| Hazard Information | Back Directory | [Uses]
2-Chloroquinoline-4-carboxylic Acid is an intermediate used to prepare dimethyl(naphthalenecarbonyl)aminobenzoic acids as potent and selective EP4 antagonists. | [Synthesis]
The general procedure for the synthesis of 2-chloroquinoline-4-carboxylic acid from 2-quinolone-4-carboxylic acid was as follows: 2-hydroxyquinoline-4-carboxylic acid (2.57 g, 13.6 mmol) was mixed with phosphorus oxytriphosphate (POCl3, 25 mL) and heated and refluxed for 24 hours. Upon completion of the reaction, the reaction mixture was quenched by slowly pouring it into crushed ice (300 g). The precipitated solid was separated by filtration, washed thoroughly with deionized water and dried under high vacuum to give 2.47 g of white solid product in 87% yield. The product was characterized by 1H NMR (CDCl3, 300 MHz) and LCMS: 1H NMR δ 8.67 (d, 1H, J = 8.4 Hz), 7.91 (d, 1H, J = 8.1 Hz), 7.83 (s, 1H), 7.67 (t, 1H, J = 7.2 Hz), 7.54 (t, 1H, J = 7.2 Hz); LCMS (m/ z): 208 ([M+H]+). | [References]
[1] Patent: WO2005/30774, 2005, A1. Location in patent: Page/Page column 23
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1837,1838
[3] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1938, vol. 125, p. 60,69 |
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