Identification | Back Directory | [Name]
4-chloroquinoline-7-carboxylic acid | [CAS]
49713-58-8 | [Synonyms]
4-chloroquinoline-7-carboxylic acid 4-chloro-7-quinolinecarboxylic acid 7-Quinolinecarboxylic acid, 4-chloro- 3-((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methylamino)benzonitrile | [EINECS(EC#)]
200-589-5 | [Molecular Formula]
C10H6ClNO2 | [MDL Number]
MFCD11518966 | [MOL File]
49713-58-8.mol | [Molecular Weight]
207.61 |
Chemical Properties | Back Directory | [Boiling point ]
364.2±27.0 °C(Predicted) | [density ]
1.469±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
3.70±0.27(Predicted) | [Appearance]
White to off-white Solid |
Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 4-chloroquinoline-7-carboxylic acid from 4-chloro-7-trifluoromethylquinoline: 10.0 g (43.2 mmol) of 4-chloro-7-trifluoromethylquinoline was dissolved in 200 mL of concentrated hydrochloric acid. The reaction was heated in a microwave reactor with radiation at 550 W power for 2 hours. Upon completion of the reaction, the reaction mixture was slowly poured into ice water and the pH was adjusted to 3-4 with sodium hydroxide solution.The precipitated product was collected by diafiltration, washed several times with deionized water and subsequently dried. Finally 8.9 g of 4-chloroquinoline-7-carboxylic acid was obtained in 99% yield of the theoretical value. Thin layer chromatography (TLC) analysis showed an Rf value of 0.45 (silica gel plate, unfolding agent was toluene/ethanol = 4:1). The molecular formula of the product was C10H6ClNO2 (molecular weight 207.62), and the mass spectrometry analysis showed that the molecular ion peak (M+H)+ was 208/210 (chlorine isotope peak). | [References]
[1] Patent: WO2004/58743, 2004, A1. Location in patent: Page/Page column 116-117 [2] Patent: WO2004/80970, 2004, A1. Location in patent: Page 34; 35 [3] Patent: WO2016/118565, 2016, A1. Location in patent: Paragraph 00320 [4] Patent: US2004/102450, 2004, A1. Location in patent: Page/Page column 72 [5] Patent: US5773449, 1998, A |
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