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Chemical Structure| 52834-10-3 Chemical Structure| 52834-10-3

Structure of 52834-10-3

Chemical Structure| 52834-10-3

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Product Details of [ 52834-10-3 ]

CAS No. :52834-10-3
Formula : C6H4Br2N2O2
M.W : 295.92
SMILES Code : O=C(O)C1=CC(Br)=NC(Br)=C1N
MDL No. :MFCD13193437

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Application In Synthesis of [ 52834-10-3 ]

* 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 [ 52834-10-3 ]

[ 52834-10-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 7579-20-6 ]
  • [ 52834-10-3 ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; bromine; acetic acid; a. 3-Amino-2,6-dibromoisonicotinic acid A slurry of 1.38 g. of 3-aminoisonicotinic acid in 25 ml. of acetic acid and cooled to 15° C. in an ice-water bath is treated dropwise with 3.2 g. of bromine in 6 ml. of the same solvent. When the addition is complete, the reaction mixture is allowed to stir at 10°-15° C. for an additional 30 min. and at room temperature for 45 min. Diethyl ether (300 ml.) is added to the reaction mixture and the resulting precipitate is filtered and dried, m.p. 251°-253° C. The free acid is liberated from the hydrobromide in the usual manner employing ammonium hydroxide.
Step 4: Preparation of 3-amino-2, 6-dibromoisonicotinic acid; 3-Aralphainoisonicotinic acid (260 mg) was dissolved in DMF (10 mL) N-bromosuccinimide (320 mg) was added and the reaction mixture was stirred at room temperature for 1 hour before another portion of N-bromosuccinimide (320 mg) was added. After stirring for 3 hours at room temperature, the reaction mixture was quenched with water. 2N Sodium hydroxide solution was added, the aqueous solution was washed 2x with diethyl ether and adjusted to pH~2 by <n="420"/>addition of 6N hydrochloric acid. The aqueous layer was extracted 3x with MTB-ether, the combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum to afford 283 mg of the title compound of the formulaas a yellow-orange solid. The compound' was contaminated with ca.10percent impurities and was used without further purification in the next step. 1H-NMR (CDCl3, TMS) delta (ppm) : 6.16 (2H, br s) , 7.61 (IH, s).
 

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