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Chemical Structure| 5381-78-2 Chemical Structure| 5381-78-2

Structure of 5381-78-2

Chemical Structure| 5381-78-2

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Product Details of [ 5381-78-2 ]

CAS No. :5381-78-2
Formula : C8H7N3O2
M.W : 177.16
SMILES Code : O=[N+](C1=CC=C2C(N=CN2C)=C1)[O-]
MDL No. :MFCD00628958

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Application In Synthesis of [ 5381-78-2 ]

* 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 [ 5381-78-2 ]

[ 5381-78-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 5381-79-3 ]
  • [ 5381-78-2 ]
  • [ 10394-38-4 ]
  • [ 26530-93-8 ]
YieldReaction ConditionsOperation in experiment
45%; 40% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 2h; General procedure: Procedure B: The nitro-group containing compound was dissolved in MeOH (or a mixture of MeOH and tetrahydrofuran) and then 10percent Pd/C was added. The mixture was stirred at room temperature under hydrogen gas until the starting material had been consumed. The crude mixture was filtered through Celite, washed with methanol, and then concentrated. The product was carried on to the next step without further purification or was purified by column chromatography.
  • 2
  • [ 5381-79-3 ]
  • [ 5381-78-2 ]
  • [ 10394-38-4 ]
  • [ 26530-93-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium 10% on activated carbon; In methanol; Powdered potassium hydroxide (5.1g, 92mmol) was added to a solution of 6-nitro-lH- benzoimidazole (3g, 18.4mmol) in acetone (30ml) in an ice bath and stirred for 30 min. Methyl iodide (1.7ml, 27.6mmol) was added and the reaction mixture was stirred for 3 hr at room temperature. The solvent was evaporated under reduced pressure to give a residue to which was added water and ethyl acetate. The organic layer was separated and washed with water, dried and concentrated to dryness to yield a mixture of 1- methyl-6-nitro-lH-benzoimidazole and l-methyl-5-nitro-lH-benzoimidazole (3.2g, 98percent) as oil. The mixture of isomers (3.2g, 18.07mmol) was dissolved in methanol (50ml) and hydrogenated at atmospheric pressure over 10percent Pd-C (300mg) until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to yield a mixture of l-methyl-lH-benzimidazol-5-yl amine and 3-methyl- 3H-benzimidazol-5-yl amine (2.53g, 95percent) as solid. The mixture was used in the next stage without purification.
  • 3
  • [ 52407-43-9 ]
  • [ 5381-78-2 ]
  • 3-methyl-3H-[1]benzofuro[2,3-b]imidazo[4,5-f]-quinoline-12-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With potassium hydroxide; In methanol; at 20℃; for 24h; General procedure: 1-Alkyl-5-nitro-1H-benzimidazole1a-1e (5 mmol) and <strong>[52407-43-9]2-(1-benzofuran-3-yl)acetonitrile</strong>(2, 0.942 g, 6 mmol) were added with stirring to a solutionof potassium hydroxide (10 g, 178 mmol) inmetha nol (30 mL). The mixture was stirred at roomtemperature for 24 h and concentrated under reducedpressure, and the precipitate was collected by filtration,washed in succession with water, cold ethanol, andacetone, and air-dried. The product was purified byrecrystallization from ethanol.3-Methyl-3H-[1]benzofuro[2,3-b]imidazo[4,5-f]-quinoline-12-carbonitrile (3a). Yield (79%), shinyyellow needles, mp 322-324C (from EtOH). IR spectrum:ν 2225 cm-1 (C≡N). 1H NMR spectrum (CDCl3),δ, ppm: 4.29 s (3H, NCH3), 7.47 t.d (1H, Harom, J = 7.8,0.7 Hz), 7.52 d (1H, Harom, J = 8.2 Hz), 7.78 t.d (1H,Harom, J = 7.8, 1.4 Hz), 8.02 d (1H, Harom, J = 9.0 Hz),8.06 d (1H, Harom, J = 9.0 Hz), 8.27 s (1H, Harom),9.02 d (1H, Harom). 13C NMR spectrum (CDCl3), δC,ppm: 31.3, 103.7, 107.6, 113.3, 114.7, 118.1, 118.8,119.2, 121.4, 122.7, 123.8, 128.3, 129.2, 135.2, 140.6,143.1, 144.0, 148.9. Mass spectrum: m/z 298 [M]+.Found, %: C 72.61; H 3.41; N 18.50. C18H10N4O.Calculated, %: C 72.48; H 3.38; N 18.78. M 298.3.
 

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