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Chemical Structure| 206257-41-2 Chemical Structure| 206257-41-2

Structure of 206257-41-2

Chemical Structure| 206257-41-2

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Product Details of [ 206257-41-2 ]

CAS No. :206257-41-2
Formula : C12H9BrClNO2
M.W : 314.56
SMILES Code : CCOC(=O)C1=C(Cl)C2=C(C=C(Br)C=C2)N=C1
MDL No. :MFCD09746288
InChI Key :NYXULZOUQJAFCL-UHFFFAOYSA-N
Pubchem ID :12052741

Safety of [ 206257-41-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H318
Precautionary Statements:P280-P301+P310-P305+P351+P338
Class:8(6.1)
UN#:2923
Packing Group:

Application In Synthesis of [ 206257-41-2 ]

* 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 [ 206257-41-2 ]

[ 206257-41-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 208580-23-8 ]
  • [ 206257-41-2 ]
YieldReaction ConditionsOperation in experiment
76% With thionyl chloride; In N,N-dimethyl-formamide;Reflux; j00381j Ethyl 7-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate (5.11 g, 17.3 mmol) was dissolved in thionyl chloride (70 mL), and DMF (0.5 mL) was added. The reactionmixture was heated to reflux overnight. The resulting solution was concentrated to provide a residue, and the residue was carefully treated with a saturated sodium carbonate solution. The resulting mixture was slurried, and then filtered. The solid isolated by filtration was washed with water, and dried in a vacuum oven to produce a yellow solid. The yellow solid was then loaded onto silica gel and purified by MPLC eluting with a gradient of 5-80% ethyl acetate inhexanes to afford ethyl 7-bromo-4-chloroquinoline-3-carboxylate as a white solid (4.12 g,76%).
76% With thionyl chloride; In N,N-dimethyl-formamide;Reflux; Ethyl 7-bromo-4-oxo- , - y roqu no ne-3-carboxylate (5.11 g, 17.3 mmol) was dissolved in thionyl chloride (70 mL), and DMF (0.5 mL) was added. The reaction mixture was heated to reflux overnight. The resulting solution was concentrated to provide a residue, and the residue was carefully treated with a saturated sodium carbonate solution. The resulting mixture was slurried, and then filtered. The solid isolated by filtration was washed with water, and dried in a vacuum oven to produce a yellow solid. The yellow solid was then loaded onto silica gel and purified by MPLC eluting with a gradient of 5-80% ethyl acetate in hexanes to afford ethyl 7-bromo-4-chloroquinoline-3-carboxylate as a white solid (4.12 g, 76%).
75% With trichlorophosphate; for 2h;Reflux; General procedure: The quinoline derivate was dispersed in POCl3 (1 mL/mmol) andheated to reflux. After 2 h the reaction mixture was poured onto ice,neutralized with satd. NaHCO3, extracted with CH2Cl2 (3×12 mL/mmol), washed with brine (1×12 mL/mmol), dried over Na2SO4, filteredand evaporated. The residue was purified by FC (gradient of 5%-15% EtOAc in LP to give the desired product.5.1.4.1. Ethyl 7-bromo-4-chloroquinoline-3-carboxylate (13a). Thechloro quinoline 13a (colorless solid, 400 mg, 75%) was obtainedfrom 12a (500 mg, 1.7 mmol) according to general procedure C; m.p.91-92 C; 1H NMR (400 MHz, DMSO-d6) delta 1.38 (t, J=7.1 Hz, 3H), 4.43(q, J=7.1 Hz, 2H), 8.00 (dd, J=9.0, 2.0 Hz, 1H), 8.30 (dd,J=9.0,1H), 8.39 (d, J=2 Hz, 1H), 9.17 (s, 1H); 13C NMR (101 MHz,DMSO-d6) delta 14.0, 62.1, 123.6, 124.3, 126.2, 127.1, 131.4, 132.2, 141.9, 149.3, 150.9, 163.6.
 

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Technical Information

Categories

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[ 206257-41-2 ]

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Related Parent Nucleus of
[ 206257-41-2 ]

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