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Chemical Structure| 1378860-76-4 Chemical Structure| 1378860-76-4

Structure of 1378860-76-4

Chemical Structure| 1378860-76-4

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Product Details of [ 1378860-76-4 ]

CAS No. :1378860-76-4
Formula : C10H8BrNO
M.W : 238.08
SMILES Code : COC1=C2C=CC=NC2=CC(Br)=C1
MDL No. :MFCD11878498
InChI Key :HPWCKYVAFXPEGG-UHFFFAOYSA-N
Pubchem ID :71237812

Safety of [ 1378860-76-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1378860-76-4 ]

* 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 [ 1378860-76-4 ]

[ 1378860-76-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1378860-76-4 ]
  • [ 1261677-80-8 ]
YieldReaction ConditionsOperation in experiment
41% Step 2: 1.5 g (0.0064 mol) of 7-bromo-5-methoxy-quinoline were refluxed with 48% HBr (30 ml) for 20h. After cooling to room temperature reaction mixture was poured into 100 ml of water and basified with saturated ammonia solution. Product was filtered off, washed with water and dried at 50C in vacuo. Yield of 7-bromo-5-hydroxy-quinoline was 600 mg (41%>).1H-NMR (400 MHz, d6-DMSO): delta(lH,s), 7.48 (lH,m), 7.18 (lH,s) ppm.
41% With hydrogen bromide; In water; for 20.0h;Reflux; Step 2:[0123]1.5 g (0.0064 mol) of 7-bromo-5-methoxy-quinoline were refluxed with 48% HBr (30 ml) for 20 h. After cooling to room temperature reaction mixture was poured into 100 ml of water and basified with saturated ammonia solution. Product was filtered off, washed with water and dried at 50??? C. in vacuo. Yield of 7-bromo-5-hydroxy-quinoline was 600 mg (41%).[0124]1H-NMR (400 MHz, d6-DMSO): ????=11.1 (1H, s(broad)), 8.88 (1H, s), 8.49 (1H, d), 7.68 (1H,USD), 7.48 (1H, m), 7.18 (1H,USD) ppm.
  • 2
  • [ 16618-68-1 ]
  • [ 56-81-5 ]
  • [ 1378860-76-4 ]
  • [ 1126824-44-9 ]
YieldReaction ConditionsOperation in experiment
27% Step 1 : 4.0g (0.02 mol) of 3-Bromo-5-methoxy-aniline, 4.6 g (0.05 mol) of glycerol, 2.46g (0.02 mol) of nitrobenzene and 12 ml of 75% sulfuric acid were stirred for 3 h at 150C. After this dark solution was poured onto 100 g of crushed ice, 100 ml of ethylacetate (EtOAc) and 30 ml of 30% solution of NaOH. After 1 hour brown solid was filtered off and the organic layer was separated. After filtering through Si02 and evaporation of solvent 7-bromo-5- methoxy-quinoline and 5-bromo-7-methoxy-quinoline were separated as mixture approximately 60:40 (total 3.5g, 74%) This mixture was separated to individual 7-bromo-5- methoxy-quinoline and 5-bromo-7-methoxy-quinoline with column chromatography on silica-gel with benzene-EtOAc (3: 1) as eluent. Yield of pure 7-bromo-5-methoxy-quinoline was 950 mg (27% from mixture).
950 mg With sulfuric acid; In water; nitrobenzene; at 150℃; for 3h; 4.1.2. Synthesis of 5-hydroxy-7-bromo-quinoline from Scheme 2[0119]The title compound can be purchased by Shanghai Haoyuan Chemexpress Co., Ltd. CHINA or synthesized via known <strong>[16618-68-1]3-bromo-5-methoxyaniline</strong> (Liedholm, Brita. Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1984), B38(10), 877-84 or Hodgson, H. H.; Wignall, J. S Journal of the Chemical Society (1926)) in two steps. 3-Bromo-5-methoxy-aniline, 4.6 g (0.05 mol) of glycerol, 2.46 g (0.02 mol) of nitrobenzene and 12 ml of 75% sulfuric acid were stirred for 3 h at 150??? C. After this dark solution was poured onto 100 g of crushed ice, 100 ml of ethylacetate (EtOAc) and 30 ml of 30% solution of NaOH. After 1 hour brown solid was filtered off and the organic layer was separated. After filtering through SiO2 and evaporation of solvent 7-bromo-5-methoxy-quinoline and 5-bromo-7-methoxy-quinoline were separated as mixture approximately 60:40 (total 3.5 g, 74%) This mixture was separated to individual 7-bromo-5-methoxy-quinoline and 5-bromo-7-methoxy-quinoline with column chromatography on silica-gel with benzene-EtOAc (3:1) as eluent. Yield of pure 7-bromo-5-methoxy-quinoline was 950 mg (27% from mixture).
 

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