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Chemical Structure| 36772-63-1 Chemical Structure| 36772-63-1

Structure of 36772-63-1

Chemical Structure| 36772-63-1

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Product Details of [ 36772-63-1 ]

CAS No. :36772-63-1
Formula : C7H4ClN3O
M.W : 181.58
SMILES Code : O=C1NN=NC2=CC(Cl)=CC=C12
MDL No. :MFCD25962790

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Application In Synthesis of [ 36772-63-1 ]

* 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 [ 36772-63-1 ]

[ 36772-63-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 5900-59-4 ]
  • [ 36772-63-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium nitrite; In water; N,N-dimethyl-formamide; at 0℃; for 1h; General procedure: Intermediates 2a-h were preparedby the similar method described in the literature [1] (Scheme 1). At 0 C, to a solution of sodium nitrite (1.38 g, 20 mmol) in 0.5 M hydrochloric acid (80 mL) was added anthranilamide 1 (10 mmol) in DMF (8 mL) over a period of 30 min. After that, the above mixture was stirred for another 1 h at 0 C. Then the mixture was basified with 30% aqueous ammonia and reacidified with hydrochloric acid to pH 2.0. The precipitate was filtered off with suction, washed with water and dried to afford the crude product, which was finally recrystallized from ethanol to yield 2.
General procedure: A solution of anthranilamide (I, 30 mmol) in DMF (15 mL) was added dropwise to a well-stirred solution of sodium nitrite (4.14 g, 60 mmol) in 0.5 M HCl (240 mL) at 0 C over a period of 40 min. After the stirring was continued at 0-5 C for 1 h, 30% aqueous ammonia was added slowly to adjust the pH to 10.0, and then reacidified to pH 2.0. After vigorously stirring for 30 min, the mixture was filtered with suction, and the filter cake was washed with water (200 mL) and dried to afford 1,2,3-benzotriazin-4-one II in yields of above 80%.
With hydrogenchloride; sodium nitrite; In water; N,N-dimethyl-formamide; at 0℃; for 1.66667h; General procedure: Compound 14 was prepared according tothe procedure previously reported.38 A solution of sodiumnitrite (4.14 g, 60 mmol) in 0.5 N HCl (240 mL) was stirred at0 C for 20 min. Anthranilamide 13 (30 mmol) dissolved inN,N-dimethylformamide (DMF, 15 mL) was then addeddropwise to the solution described above for 40 min. Afterthe mixture had been stirred for an additional 1 h at 0 C, 30%aqueous ammonia was added slowly to adjust the pH to 10.0.The reaction mixture was allowed to stir for 15 min and thenreacidified to pH 2.0. After the mixture had been stirred for 30min, the precipitated product was filtered off with suction,washed with water (200 mL), and dried to afford compound 14in yields of 75-83%.
General procedure: A solution of anthranilamide (30 mmol) in 1 N HCl (120 mL) was stirred at 0 C for 20 min. Then, sodium nitrite (60 mmol) dissolved in deionized water (100 mL) was added dropwise to the above solution for 40 min. After another 2 h of stirring at 0 C, 30% NaOH solution was added slowly to adjust the pH to 8.0. The reaction mixture was allowed to stir vigorously for 15 min. The precipitated product was filtered off with suction, washed with deionized water (200 mL), and dried to afford compound 4 in yield of 82%.
General procedure: A solution of anthranilamide (30 mmol) in 1N HCl (120 mL) was stirred at 0 C for 20 min. Then, sodium nitrite (60 mmol) dissolved in deionized water (100 mL) was added dropwise to the above solution for 40 min. After another 2 h of stirringat 0 C, 30% NaOH solution was added slowly to adjustp H value to 8.0. The reaction mixture was allowed to stir vigorously for 15 min. The precipitated product was filtered, washed with deionized water (200 mL), and dried to afford compounds 10 in yields of 40-92%.

 

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