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Chemical Structure| 1222184-73-7 Chemical Structure| 1222184-73-7

Structure of 1222184-73-7

Chemical Structure| 1222184-73-7

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Product Details of [ 1222184-73-7 ]

CAS No. :1222184-73-7
Formula : C7H4BrNO4
M.W : 246.02
SMILES Code : O=C(C1=NC=CC(C(O)=O)=C1Br)O

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Application In Synthesis of [ 1222184-73-7 ]

* 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 [ 1222184-73-7 ]

[ 1222184-73-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 27063-93-0 ]
  • [ 1222184-73-7 ]
YieldReaction ConditionsOperation in experiment
Dimethyl 3-bromopyridine-2,4-dicarboxylate 113-Bromo-2,4-lutidine 10 (7.00 g, 38 mmol, 1 eq.) and water (100 mL) were heated to 100 0C, and a solution of NaOH (1.05 g, 26 mmol, 0.7 eq.) in water (15O mL) was added. KMnO4 (29.7 g, 188 mmol, 5 eq.) was then added in portions over 30 min under vigorous stirring. The resulting dark suspension was stirred under reflux until the colour of KMnO4 had vanished completely (2-3 h, determined in 3 independent experiments). The hot solution was filtered and solids washed with hot water (3 * 50 mL). The filtrate was concentrated to ca. 50 mL in vacuo and neutralised with cone. H2SO4. The solution was concentrated in vacuo, the residue was coevaporated with toluene and suspended in MeOH (200 mL). Cone. H2SO4 (10 mL) was added, the resulting suspension was refluxed overnight and then cooled to room temperature and concentrated in vacuo. The residue was taken up in water, the pH was adjusted to pH 9 by careful addition Of Na2CO3 and the basic solution was extracted with EtOAc (3 x 100 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was purified by automated column chromatography (Biotage KP-SIL.(TM). SNAP 100 g cartridge) to afford 11 (4.62 g, 45percent) as a white solid.1H NMR deltaH (400 MHz; CDCl3) 3.98 (s, 3H, OCH3), 4.01 (s, 3Eta, OCH3), 7.60 (d, J=5.0 Hz, IH, pytfortho), 8.64 (d, J=5.0 Hz, IH, pyHmeta); 13C NMR deltac (100 MHz; CDCl3) 53.2 (CH3), 53.3 (CH3), 115.6 (ArC), 125.2 (ArCH), 142.1 (ArC), 148.0 (ArCH), 152.4 (ArC), 164.9 (CO), 165.4 (CO); IR vmax (KBr diskycm"1 3019, 2958, 1743, 1449, 1421, 1279, 1202, 1171; HRMS (ESI+) for C9H8BrNNaO4 requires 295.9529, found (M+Na+) 295.9524; Microanalysis for C9H8BrNO4 requires C 39.44, H 2.94, N 5.11; found C 39.54, H 2.95, N 5.02;
 

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