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[ CAS No. 5350-47-0 ] {[proInfo.proName]}

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Chemical Structure| 5350-47-0
Chemical Structure| 5350-47-0
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CAS No. :5350-47-0 MDL No. :
Formula : C14H11NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 241.24 Pubchem ID :-
Synonyms :

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* 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.

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[ 5350-47-0 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 5350-47-0 ]
  • [ 7377-13-1 ]
YieldReaction ConditionsOperation in experiment
85% With chromium(VI) oxide; sulfuric acid In acetic acid at 0 - 20℃; To an ice-cooled mixture of 6 (20.00 g, 0.08 mol) in glacial acetic acid (150 mL) was added sulfuric acid (28 mL) slowly to keep the temperature below 5 °C. Chromium oxide (28.00 g, 0.28 mol) was added in small portions at such a rate that the temperature did not exceed 10 °C. The reaction solution was stirred at room temperature overnight, then ice water (20 mL) was added. The precipitated solid was filtered, washed with water and dried to afford 7 22.0 g (85percent) of a white powder. mp 254-256 °C.
60% for 4 h; Reflux A mixture of (4-nitrophenyl)(4-tolyl)methanone (12c) (0.50 g, 2.0 mmol) and Jones reagent (0.7 ml) in glacial acetic acid (4 ml) was heated under reflux for 4 h. The reaction mixture was then poured on crushed ice, and extracted with ethyl acetate (10 ml) three times. The organic layer was washed with water until the washings became neutral and was extracted with 10percent NaHCO3 (2 .x. 20 ml). The aqueous extract was acidified with concentrated HCl to pH 3. The solid that formed was filtered off and dried. Yield (0.337 g, 60percent), m.p. 256-257 °C (lit.24 m.p. 255 °C). 1H NMR (300 MHz, (CD3)2SO): d 8.37 (d, J = 8.8 Hz, 2H), 8.05 (d, J = 8.4 Hz, 2H), 7.96 (d, J = 8.8 Hz, 2H), 7.78 (d, J = 8.4 Hz, 2H). 13C NMR (75 MHz, (CD3)2SO): d 194.42, 167.43, 149.47, 142.43, 137.48, 130.75, 129.58, 129.28, 129.03, 123.69.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1036 - 1039
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 748 - 759
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 380 - 386
[4] Justus Liebigs Annalen der Chemie, 1895, vol. 286, p. 329
[5] Molecular crystals and liquid crystals, 1984, vol. 111, # 3-4, p. 255 - 266
[6] Medicinal Chemistry, 2013, vol. 9, # 2, p. 294 - 302
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