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Structure of 203794-33-6

Chemical Structure| 203794-33-6

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Product Details of [ 203794-33-6 ]

CAS No. :203794-33-6
Formula : C5H3Cl2N3O2
M.W : 208.00
SMILES Code : NC1=NC(Cl)=C(Cl)C=C1[N+]([O-])=O
MDL No. :MFCD22987594
InChI Key :DYSLEQUCBXITJX-UHFFFAOYSA-N
Pubchem ID :15392047

Safety of [ 203794-33-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 203794-33-6 ]

* 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 [ 203794-33-6 ]

[ 203794-33-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 5409-39-2 ]
  • [ 203794-33-6 ]
YieldReaction ConditionsOperation in experiment
With N-chloro-succinimide; acetic acid; at 80℃; INTERMEDIATE 16-οΜθΓθ-5-οο-2-( 6ν3^ηγ1>-1Η-^8ζο f4,5-b1 pyridineStep A 5, 6-dichloro-3 -nitropyridin-2-amine. To a solution of <strong>[5409-39-2]5-chloro-3-nitropyridin-2-amine</strong> (16 g, 92 mmol) in AcOH (70 mL) was added N-chlorosuccinimide (14.8 g i l l mmol). The mixture was stirred overnight at 80 C for 3 h, cooled to rt, diluted with MeOH (30 mL) and filtered. The solid residue was washed with AcOH, water, and then dried to afford the desired product as a white solid, which was used in the next step without further purification. LC-MS: calculated for C5H3Cl2N302 208.0, observed m/e: 208.07 (M+H)+ (Rt 1.48/5 min).
With N-chloro-succinimide; acetic acid; at 80℃; for 3h; To a solution of <strong>[5409-39-2]5-chloro-3-nitropyridin-2-amine</strong> (16 g, 92 mmol) in AcOH (70 mL) was added N-chlorosuccinimide (14.8 g 111 mmol). The mixture was stirred overnight at 80 C. for 3 h, cooled to rt, diluted with MeOH (30 mL) and filtered. The solid residue was washed with AcOH, water, and then dried to afford the desired product as a white solid, which was used in the next step without further purification. LC-MS: calculated for C5H3Cl2N3O2 208.0, observed m/e: 208.07 (M+H)+ (Rt 1.48/5 min).
With N-chloro-succinimide; acetic acid; at 80℃; for 3h; Step A 5,6-dichioro-3-nitropyridin-2-amine10552] To a solution of <strong>[5409-39-2]5-chloro-3-nitropyridin-2-amine</strong> (16 g, 92 mmol) in AcOR (70 mE) was added N-chlorosuccinimide (14.8 g 111 mmol). The mixture was stirred overnight at 80 C. for 3 h, cooled to rt, diluted with MeOR (30 mE) and filtered. The solid residue was washed with AcOR, water, and then dried to afford the desired product as a white solid, which was used in the next step without thrther purification. EC-MS: calculated for C5H3C12N302 208.0. observed mle: 208.07 (M+H) (Rt 1.48/5 mm).
With N-chloro-succinimide; acetic acid; at 80℃; To a solution of <strong>[5409-39-2]5-chloro-3-nitropyridin-2-amine</strong> (16 g, 92 mmol) in AcOH (70 mL) was added N-chlorosuccinimide (14.8 g 111 mmol). The mixture was stirred overnight at 80 C. for 3 h, cooled to rt, diluted with MeOH (30 mL) and filtered. The solid residue was washed with AcOH, water, and then dried to afford the desired product as a white solid, which was used in the next step without further purification. LC-MS: calculated for C5H3Cl2N3O2 208.0, observed m/e: 208.07 (M+H)+ (Rt 1.48/5 min)
With N-chloro-succinimide; acetic acid; at 80℃; for 3h; To a solution of <strong>[5409-39-2]5-chloro-3-nitropyridin-2-amine</strong> (16 g, 92 mmol) in AcOH (70 mL) was added N-chlorosuccinimide (14.8 g 111 mmol). The mixture was stirred overnight at 80 C. for 3 h, cooled to rt, diluted with MeOH (30 mL) and filtered. The solid residue was washed with AcOH, water, and then dried to afford the desired product as a white solid, which was used in the next step without further purification. LC-MS: calculated for C5H3Cl2N3O2 208.0, observed m/e: 208.07 (M+H)+ (Rt 1.48/5 min).
With N-chloro-succinimide; acetic acid; at 80℃; for 3h; To a solution of <strong>[5409-39-2]5-chloro-3-nitropyridin-2-amine</strong> (16 g, 92mmol) in AcOR (70 mE) was added N-chlorosuccinimide(14.8 g 111 mmol). The mixture was stirred overnight at 80 C. for 3 h, cooled to rt, diluted with MeOR (30 mE) and filtered. The solid residue was washed with AcOR, water, and then dried to afford the desired product as a white solid,which was used in the next step without further purification. EC-MS: calculated for C5H3C12N302 208.0. observed mle:208.07 (M+H) (Rt 1.48/5 mm).

  • 2
  • [ 1192814-45-1 ]
  • [ 203794-33-6 ]
YieldReaction ConditionsOperation in experiment
62% With sulfuric acid; nitric acid; at -10 - 20℃; for 0.666667h; Aminopyridine 5 (1.20g, 7.26mmol) was dissolved in c.H2SO4 (11mL) upon stirring in an ice/salt bath, followed by dropwise addition of HNO3 (65%, 1.15mL) at -10C. The reaction was subsequently stirred at room temparature for 40min. Then, the reaction mixture was poured into ice and neutralized with an ammonium hydroxide solution, adjusting the pH to 6. The precipitate was filtrered and the dry residue was subjected to column chromatography (silica gel 60-200μm) and eluted with DCM/MeOH (99.5/0.5, v/v). Evaporation of the appropriate fractions afforded 951mg (62%) of 6. mp 186-187C (EtOAc). 1H NMR and ΜS data previously reported [42].
 

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