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Structure of 10394-38-4

Chemical Structure| 10394-38-4

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Product Details of [ 10394-38-4 ]

CAS No. :10394-38-4
Formula : C8H9N3
M.W : 147.18
SMILES Code : NC1=CC=C2C(N=CN2C)=C1
MDL No. :MFCD03164349
Boiling Point : No data available
InChI Key :IWBGBYZGEQUDBT-UHFFFAOYSA-N
Pubchem ID :315499

Safety of [ 10394-38-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 10394-38-4 ]

* 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 [ 10394-38-4 ]

[ 10394-38-4 ] Synthesis Path-Downstream   1~4

  • 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
  • [ 51-17-2 ]
  • [ 74-88-4 ]
  • [ 10394-38-4 ]
  • [ 26530-93-8 ]
YieldReaction ConditionsOperation in experiment
Granular tin, 16 g (0.135 mol), was added to 100 mL of concentrated aqueous HCl, and 8.85 g (0.05 mol) of isomer mixture 2/3 was carefully added in portions. The addition of each portion was accompanied by vigorous reaction with strong heat evolution. When the addition was complete, the hot transparent solution was separated by decanting from the tin residue. After cooling, tin salt of 4/5 precipitated and was filtered off and dispersed in 200 mL of propan-2-ol, solid potassium hydroxide was added until weakly alkaline reaction, the precipitate of Sn(OH)2 was filtered off, and the filtrate was evaporated to dryness. The residue, light brown crystals of isomeric amines 4 and 5, was used in the next step without purification. Yield 6.55 g (89percent), mp 113-114°C. IR spectrum, nu, cm?1: 3376 (NH2, asym.), 3203 (NH2, sym.). 1H NMR spectrum, delta, ppm: isomer 4: 3.81 s (3H, NCH3), 6.62 s (2H, NH2), 6.77 d (1H, 6-H, J = 8.4 Hz), 6.86 d (1H, 7-H, J = 8.4 Hz), 7.30 s (1H, 4-H), 8.49 s (1H, 2-H); isomer 5: 3.69 s (3H, NCH3), 6.59 s (2H, NH2), 6.77 s (1H, 7-H), 6.86 d (1H, 5-H, J = 8.4 Hz), 7.38 d (1H, 4-H, J = 8.4 Hz), 8.08 s (1H, 2-H). Found, percent: C 64.95; H 5.91; N 28.67. C8H9N3. Calculated, percent: C 65.29; H 6.16; N 28.55.
  • 4
  • [ 94-52-0 ]
  • [ 74-88-4 ]
  • [ 10394-38-4 ]
  • [ 26530-93-8 ]
YieldReaction ConditionsOperation in experiment
To a suspension of NaH (0.883 g) in Nu,Nu-dimethylformamide (DMF) (20 mL) at 0 °C was added 6-nitro-1 H-benzo[d]imidazole (2 g) and methyl iodide (2.3 mL). The reaction mixture was warmed to room temperature for 2 h . The reaction mixture was then poured into ice/water (30 mL). The solid were filtered and dried under reduced pressure to afford a mixture of 1 -methyl-6-nitro-1 H-benzo[d]imidazole and 1 -methyl-5-nitro-1 H- benzo[d]imidazole (1 g) as a yellow solid. LCMS m/z 178.12 (M+H)+. To a suspension of Pd/C (0.601 g, 0.564 mmol) in methanol (20 mL) at room temperature was added the mixture of 1 -methyl-6-nitro-1 H-benzo[d]imidazole and 1 -methyl-5-nitro-1 H- benzo[d]imidazole (1 g). The reaction was placed under hydrogen (1 atm) for 16 h. The reaction mixture was then filtered through a pad of celite and was concentrated to afford a mixture of 1 -methyl-1 Hbenzo[d]imidazol-6-amine and 1 -methyl-1 H-benzo[d]imidazol-5- amine (500 mg) as a brown solid. LCMS m/z 148.0 (M+H)+.
 

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[ 10394-38-4 ]

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