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Chemical Structure| 65795-95-1 Chemical Structure| 65795-95-1

Structure of 65795-95-1

Chemical Structure| 65795-95-1

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Product Details of [ 65795-95-1 ]

CAS No. :65795-95-1
Formula : C15H12N2O2
M.W : 252.27
SMILES Code : O=[N+](C1=CC2=C(N(CC3=CC=CC=C3)C=C2)C=C1)[O-]
MDL No. :MFCD03206550
InChI Key :LONPVIGEVNTHTN-UHFFFAOYSA-N
Pubchem ID :9856351

Safety of [ 65795-95-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 65795-95-1 ]

* 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 [ 65795-95-1 ]

[ 65795-95-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 65795-95-1 ]
  • [ 26807-73-8 ]
YieldReaction ConditionsOperation in experiment
63% With iron; acetic acid; In methanol; at 65℃; for 2.0h; 1-benzyl-5-nitro-1H-indole (500 mg, 1.98 mmol, 1.0 equiv.), reducing iron powder (555 mg,9.9 mmol, 5.0 equiv.) dissolved in an appropriate amount of MeOH, and added with stirring AcOH (594 mg, 9.9 mmol, 5.0 equiv.) at 65Stir at C for 2 hours. The TLC monitors the reaction in real time. After the reaction, the reaction solution was filtered through celite, washed with methanol, and distilled under reduced pressure.The crude product was purified by silica gel column chromatography toield of 1-benzyl-1H-indole-5-amine (280 mg, yield: 63%).
22.4 g With water; iron; ammonium chloride; In ethanol; at 70 - 75℃; for 3.5h;Reflux; [Reference Example 12] (0454) (0455) To the mixture of 45.5 g of 1-benzyl-5-nitro-1H-indole, 6.15 g of ammonium chloride, 360 mL of ethanol and 90 mL of water, 35.2 g of iron powder was added in portions at an external temperature of 70 to 75C, and the resultant was heated at reflux for three hours and 30 minutes. After cooling the reaction mixture to room temperature, water and ethyl acetate were added thereto, and the insoluble matter was filtered off. The filter cake was washed with water and ethyl acetate. The filtrate and the washings were combined, the organic layer was separated, sequentially washed with water and a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Diisopropyl ether and ethyl acetate were added to the obtained residue and the solid was collected by filtration. The obtained solid was purified by silica gel column chromatography (gradient elution with hexane:ethyl acetate = 90:10-50:50), and hexane was added to the thus obtained residue, and the solid was collected by filtration to give 22.4 g of 1-benzyl-1H-indol-5-amine as a pale brown solid. 1H-NMR (DMSO-d6) delta: 4.47 (2H, s), 5.27 (2H, s), 6.17 (1H, d, J = 2.6 Hz), 6.47 (1H, dd, J = 8.6, 2.0 Hz), 6.68 (1H, d, J = 2.0 Hz), 7.08 (1H, d, J = 8.6 Hz), 7.12-7.17 (2H, m), 7.21-7.32 (4H, m).
 

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