| Identification | Back Directory | [Name]
7-CHLOROQUINOLINE | [CAS]
612-61-3 | [Synonyms]
7-CHLOROQUINOLINE
Quinoline, 7-chloro-
7-Chloro-4-nitroquinoline
7-Chloro-1-azanaphthalene | [EINECS(EC#)]
-0 | [Molecular Formula]
C9H6ClN | [MDL Number]
MFCD00956370 | [MOL File]
612-61-3.mol | [Molecular Weight]
163.6 |
| Chemical Properties | Back Directory | [Melting point ]
31.5°C | [Boiling point ]
268°C(lit.) | [density ]
1.2158 | [refractive index ]
1.6108 (estimate) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Acetone (Slightly), Chloroform (Slightly) | [form ]
Solid | [pka]
3.36±0.14(Predicted) | [color ]
Tan | [λmax]
319nm(EtOH aq.)(lit.) | [NIST Chemistry Reference]
7-chloroquinoline(612-61-3) |
| Hazard Information | Back Directory | [Chemical Properties]
light yellow powder | [Uses]
Chloroquinolines block antibiotic efflux pumps in antibiotic-resistant Enterobacter aerogenes isolates. | [Synthesis]
General Program 138: Synthesis of 7-chloroquinoline (Intermediate 573)
1. 4,7-Dichloroquinoline (10 g, 50 mmol) was dissolved in THF (100 ml) and degassed using N2 for 5 min.
2. PdCl2 (dppf) (1.2 g, 2 mmol), TMEDA (9.97 g, 86 mmol) and NaBH4 (3.24 g, 86 mmol) were added sequentially.
3. The reaction mixture was stirred at room temperature for 5 hours.
4. Upon completion of the reaction, brine (20 ml) was added dropwise followed by removal of solvent under vacuum.
5. The residue was dissolved in EtOAc (200 ml), dried by adding MgSO4 and then concentrated under vacuum.
6. The crude product was purified by column chromatography using heptane/EtOAc (4:1 to 1:1 gradient) as eluent to afford the title compound 7-chloroquinoline (5.4 g, 65% yield).
MW: 163.61
HPLCMS (Method B): [m/z]: 163.90 | [References]
[1] Tetrahedron Letters, 2010, vol. 51, # 12, p. 1562 - 1565
[2] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 191 - 209
[3] Patent: US2012/214803, 2012, A1. Location in patent: Page/Page column 185 |
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