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Chemical Structure| 4225-86-9

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Product Details of [ 4225-86-9 ]

CAS No. :4225-86-9
Formula : C9H5ClN2O2
M.W : 208.60
SMILES Code : [O-][N+](=O)C1=CC=CC2=C1N=C(Cl)C=C2
MDL No. :MFCD00160589
InChI Key :RVJHLZFALCBCIW-UHFFFAOYSA-N
Pubchem ID :319453

Safety of [ 4225-86-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 4225-86-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4225-86-9 ]

[ 4225-86-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 612-62-4 ]
  • [ 13067-94-2 ]
  • [ 4225-86-9 ]
YieldReaction ConditionsOperation in experiment
14%; 54% Pure H2SO4 was added onto 1 equiv of 29 at 0 C. 3 equiv of 65% HNO3 were then added dropwise and the reaction mixture was stirred at rt for 1 h. After the reaction mixture was poured into water, the solution was neutralized with Na2CO3 and extracted twice with dichloromethane. The organic layer was washed with water, dried over anhydrous Na2SO4 and evaporated in vacuo.Compound 30 was obtained, after purification by column chromatography (eluent: cyclohexane-ethyl acetate 8:2), as a white solid in 54% yield; mp 152 C, Lit: 149 C [40]. 1H NMR (200 MHz, CDCl3) delta: 7.52-7.56 (d, J = 8.6 Hz, 1H), 7.60-7.68 (m, 1H), 8.02-8.11 (m, 2H), 8.20 (d, J = 8.6 Hz, 1H). 13C NMR (50 MHz, CDCl3) delta: 124.6 (CH), 124.9 (CH), 125.8 (CH), 127.6 (C), 131.8 (CH), 138.6 (CH), 139.0 (C), 147.3 (C), 153.6 (C).Compound 31 was obtained, after purification by column chromatography (eluent: cyclohexane-ethyl acetate 8:2), as a pale yellow solid in 14% yield; mp 134 C, Lit: 133-134 C [41]. 1H NMR (200 MHz, CDCl3) delta: 7.63 (d, J = 9.2 Hz, 1H), 7.80-7.88 (m, 1H), 8.34 (d, J = 8.5 Hz, 1H), 8.40 (dd, J = 1.1 and 7.7 Hz, 1H), 8.99 (d, J = 9.2 Hz, 1H). 13C NMR (50 MHz, CDCl3) delta: 119.9 (C), 124.9 (CH), 125.4 (CH), 128.8 (CH), 134.9 (CH), 135.5 (CH), 145.4 (C), 148.0 (C), 152.5 (C).
14%; 50% With sulfuric acid; nitric acid; In water; at 0 - 20℃; for 2.0h; General procedure: H2SO4 (98%) was added onto 1 equiv. of the quinoline derivatives, cooled with an ice bath. 5 equiv. of 65% HNO3 were then added dropwise at 0 C and the reaction mixture was stirred at rt for 1-4 h. The reaction mixture was successively poured into ice, neutralized with NaOH and extracted three times with dichloromethane. The organic layer was washed with water, dried over anhydrous Na2SO4 and evaporated in vacuo. The crude residue was purified by chromatography on silica gel using adapted eluent and recrystallized if necessary to give compounds 1, 4, 6, 12, 15, 17 and 18. 8-nitroquinoline 1 (C9H6N2O2) was purified by chromatography on silica gel using dichloromethane as an eluent, separated from its 5-nitro isomer and isolated to yield a pale yellow solid (35%, 2.7 mmol, 470 mg).
  • 2
  • [ 612-62-4 ]
  • HNO3+H2SO4 [ No CAS ]
  • [ 13067-94-2 ]
  • [ 4225-86-9 ]
 

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