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Chemical Structure| 55577-25-8

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Product Details of [ 55577-25-8 ]

CAS No. :55577-25-8
Formula : C15H13N
M.W : 207.27
SMILES Code : CC1=CC=C(C(N2)=CC3=C2C=CC=C3)C=C1
MDL No. :MFCD00087262
InChI Key :VPXGIHGJJJBJFP-UHFFFAOYSA-N
Pubchem ID :292599

Safety of [ 55577-25-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 55577-25-8 ]

* 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 [ 55577-25-8 ]

[ 55577-25-8 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 55577-25-8 ]
  • (E)-2-p-tolyl-3H-indol-3-one oxime [ No CAS ]
  • 2
  • [ 122-00-9 ]
  • [ 100-63-0 ]
  • [ 55577-25-8 ]
YieldReaction ConditionsOperation in experiment
30% With acetic acid; zinc(II) chloride; In neat (no solvent); at 25 - 180℃; for 0.416667h; General procedure: Phenylhydrazine 1a (5.1 mmol) and acetophenone 2a (5 mmol) and anhydrous zinc chloride (200 mol %) were mixed together using pestle in mortar and few drops ofacetic acid (0.1 N) was added drop-wise with continuous mixing at room temperature for 10 min. The mixture was transferred into a round-bottomed flask fitted with a reflux condenser attached with CaCl2 guard tube. Then the mixture was heated slowly up to the temperature of 180 C. The reaction was monitored by TLC using 10% ethyl acetatein n-hexane and the reaction was observed to be completed within 15 min. The mixture was cooled to room temperature and diluted with 5mL dichloromethane and 5mL water. The dichloromethane layer was separated and aqueous layer extracted repeatedly with dichloromethane (3 x 5mL). The combined organic layer was dried over anhydrous Na2SO4, filtered, and solvent was evaporated under reduced pressure. The crude product was purified using flash column chromatography over silica gel using 6% ethyl acetate in hexane as eluent to afford the pure product 2-phenylindole 4a in 86% yield as light yellow solid (Table 1, entry 1).
General procedure: Appropriate amounts of substituted acetophenone 3 (1 mmol) and phenyl hydrazine (1 mmol) were mixed in ethanol (20 mL), and a few drops of glacial acetic acid were added. The solution was heated under reflux at 80 C for 1-2 h. The solvent was evaporated in vacuo to give a solid that was added to polyphosphoric acid (PPA) (30 mL), and the mixture was slowly heated to 120 C and kept at this temperature for a few hours until the reaction was complete (TLC monitoring). The mixture was allowed to cool and then poured into cold water (50 mL). The acidic solution was neutralized by the slow addition of NaOH (1 M), and the solid precipitate of the crude product was collected. Purification by column chromatography (hexane/ethyl acetate) gave the substituted 2-aryl indoles 4a-g.
General procedure: Appropriate amounts of substituted acetophenone 1 (1 mmol) and phenyl hydrazine2 (1 mmol) were mixed in ethanol (20 mL), and a few drops of glacial acetic acid were added. The solution was heated under reflux at 80 C for 1-2 h. The solvent was evaporated in vacuo to give a solid that was added to polyphosphoric acid (30 mL), and the mixture was slowly heated to 120 C and kept at this temperature for a few hours until the reaction was complete (TLC monitoring). The mixture was allowed to cool and then poured into cold water (50 mL). The acidic solution was neutralized by the slow addition of NaOH (1 M), and the solid precipitate of the crude product was collected. Purification by column chromatography (hexane/ethyl acetate) gave the substituted 2-aryl indoles 3a-f.
With methanesulfonic acid; acetic acid; at 80℃; General procedure: P-substituted acetophenone (2mmol) and phenyl-hydrazine (2mmol) were poured into a round bottom flask, then CH3COOH (0.5mL) and CH4O3S (27mmol) were added. After the thin layer chromatography (TLC) monitoring reaction was completed, the intermediate 3 was obtained by pouring the mixture into ice water. At -30C, POCl3 (10mmol) was slowly added dropwise to a round bottom flask containing DMF (10mmol), and the reaction was stirred for 1h. After that, intermediate 3 (1mmol) was dissolved in DMF, slowly added dropwise to the flask, and the reaction was heated to 70C with stirring. Monitor the reaction through the TLC. Finally, the mixture was poured into ice water, washed with 40% NaOH solution, and then extracted with DCM to obtain intermediate 4.

  • 5
  • N-<<(Trimethylsilyl)ethoxy>methyl>-2-(4-toluyl)indole [ No CAS ]
  • [ 55577-25-8 ]
  • 7
  • [ 55577-25-8 ]
  • [ 33513-42-7 ]
  • [ 68945-00-6 ]
YieldReaction ConditionsOperation in experiment
89% With trichlorophosphate; at 10 - 45℃; for 0.5h; General procedure: Compounds 10a-f were synthesized by known procedure. A solution of 2-aryl-1H-indole 9a-f (0.01 mol) in a minimum amount of DMF was added to the Vilsmeier-Haack reagent (was prepared from phosphorus oxychloride (1 mL) and DMF(3.15 mL)) maintaining the reaction temperature between 10 and 20 C. The reaction mixture was heated at 45 C for 30 min and poured into a mixture of ice-water (100 mL) and 10% aqueous NaOH (20 mL). The resulting mixture was refl uxed for 1 h and cooled to room temperature. The precipitate was collected by filtration, washed with water, dried, and recrystallized.
88% General procedure: Under nitrogen gas, phosphorous oxychloride (10 mmol) was added dropwise to dry dimethylformamide (DMF) (10 mmol) while cooling in an ice bath, and the reaction mixture was stirred for 1 h. A solution of compound 4 (1 mmol) in DMF (50 ml) was added dropwise to the mixture with continuous stirring, which was then heated to 70 C. The mixture was poured onto ice cold water (200 mL), naturalized with 40% NaOH, and extracted with chloroform. The chloroform extract was washed with water and dried over Na2SO4. The solvent was removed under vacuum. The residue was crystalized from an ethanol/water mixed solvent system.
88% With trichlorophosphate; at 70℃;Inert atmosphere; General procedure: Under nitrogen gas, phosphorous oxychloride (10 mmol) was added dropwise to dry dimethylformamide (DMF) (10 mmol) while cooling in an ice bath, and the reaction mixture was stirred for 1 h. A solution of compound 3 (1 mmol) in DMF (50 ml) was added dropwise to the mixture with continuous stirring, which was then heated to 70 C. The mixture was poured onto ice cold water (200 mL), naturalized with 40% NaOH, and extracted with chloroform. The chloroform extract was washed with water and dried over Na2SO4.The solvent was removed under vacuum. The residue was crystalized from an ethanol/water mixed solvent system [27].
General procedure: P-substituted acetophenone (2mmol) and phenyl-hydrazine (2mmol) were poured into a round bottom flask, then CH3COOH (0.5mL) and CH4O3S (27mmol) were added. After the thin layer chromatography (TLC) monitoring reaction was completed, the intermediate 3 was obtained by pouring the mixture into ice water. At -30C, POCl3 (10mmol) was slowly added dropwise to a round bottom flask containing DMF (10mmol), and the reaction was stirred for 1h. After that, intermediate 3 (1mmol) was dissolved in DMF, slowly added dropwise to the flask, and the reaction was heated to 70C with stirring. Monitor the reaction through the TLC. Finally, the mixture was poured into ice water, washed with 40% NaOH solution, and then extracted with DCM to obtain intermediate 4.

  • 8
  • [ 823809-32-1 ]
  • [ 55577-25-8 ]
  • 9
  • [ 120-72-9 ]
  • [ 624-31-7 ]
  • [ 55577-25-8 ]
YieldReaction ConditionsOperation in experiment
90% With palladium; anhydrous Sodium acetate; In dimethyl sulfoxide; at 120℃; for 24h;Catalytic behavior; General procedure: The DMSO (3 mL) were added in to the ovendried 25 mL R.B.F containing compound 1a (58.57 mg,0.5 mmol, 1 equiv), followed by addition of NaOAc(45.11 mg, 1.1 equiv), Pd NPs (2.39 mg, 2 mol% Pd content:44.48 w/w), iodobenzene 2a (408.02 mg, 2 mmol, 4 equiv).The reaction mixture was stirred at 120 C for 24 h, aftercomplete conversion of starting material (indicated by TLC),the reaction was quenched with water and the organic layerwas extracted with EtOAc (25 × 3) the combined organiclayer was dried over anhydrous Na2SO4the solvent wasevaporated by rotary evaporator and crude compound waspurified by column chromatography (eluent: 2% EA/Hexane)to get the compound 2-phenyl-1H-indole (3a, 88.01 mg,92%).
  • 12
  • [ 615-43-0 ]
  • [ 122-00-9 ]
  • [ 55577-25-8 ]
YieldReaction ConditionsOperation in experiment
60% General procedure: Potassium tert-butoxide (1.14 g, 10.2 mmol) was added to a stirred solution of the acetophenone (10 mmol) in anhydrous and oxygen-free DMSO. The mixture was stirred for 15 min., when 2-iodoaniline (0.657 g, 3.0 mmol) was added and the reaction was subjected to irradiation with a 400 W mercury lamp. After 3 h, water (50 mL) was added and the reaction products were extracted with CH2Cl2 (2 × 30 mL). The combined organic phases were successively washed with water (20 mL) and brine (20 mL), dried over MgSO4, and the solvent was removed under reduced pressure. The products were obtained in pure form after crystallization from a 20:80 mixture of Et2O and petroleum ether.
  • 13
  • [ 51270-89-4 ]
  • [ 95-51-2 ]
  • [ 55577-25-8 ]
  • 14
  • [ 51270-89-4 ]
  • [ 615-36-1 ]
  • [ 55577-25-8 ]
  • 15
  • [ 615-43-0 ]
  • [ 766-97-2 ]
  • [ 55577-25-8 ]
YieldReaction ConditionsOperation in experiment
74% General procedure: A dry sealed tube was charged with 1.1 mmol (271 mg) of 2-iodoaniline and 2 equiv. of K3PO4 (424 mg). To the above mixture was added 1 mmol of phenylacetylene (102 mg, 0.109 ml), 5 mol % of Et2Zn (0.05 ml), 10 mol % of DMEDA (0.01 ml) and 3 ml of acetonitrile under nitrogen. The sealed tube was heated in an oil bath which was preheated to 125 C and the reaction mixture was stirred under the same conditions for 12 hours. After that 2 equiv. of NaOtBu (192 mg) was added to the reaction mixture and allowed to stir for another six hours. The reaction mixture was then cooled and extracted with ethyl acetate (3 x 15 ml) and the ethyl acetate layer was washed with distilled water. The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure in a rotary evaporator. The crude residue was purified by column chromatography using hexane as the eluent to get 172 mg (89 %) of the product as a colourless solid. All other benzofuran derivatives were synthesized by similar procedure.
  • 16
  • [ 55577-25-8 ]
  • [ 16523-54-9 ]
  • N-(dicyclohexylphosphino)-2-(4'-tolyl)-1H-indole [ No CAS ]
  • 19
  • [ 5720-05-8 ]
  • [ 167558-54-5 ]
  • [ 55577-25-8 ]
  • 23
  • [ 201230-82-2 ]
  • [ 124643-45-4 ]
  • [ 55577-25-8 ]
  • [ 90828-09-4 ]
  • 24
  • [ 120-72-9 ]
  • [ 5720-05-8 ]
  • [ 55577-25-8 ]
  • [ 30015-86-2 ]
  • 25
  • [ 4248-19-5 ]
  • [ 38175-73-4 ]
  • [ 55577-25-8 ]
  • 26
  • [ 55577-25-8 ]
  • [ 501-65-5 ]
  • [ 1224200-02-5 ]
  • 27
  • [ 1224876-13-4 ]
  • [ 55577-25-8 ]
  • 31
  • [ 55577-25-8 ]
  • [ 488-48-2 ]
  • [ 1394077-19-0 ]
YieldReaction ConditionsOperation in experiment
77% With potassium carbonate; In acetonitrile; at 20℃; for 6h; General procedure: A mixture of chloranil or p-bromanil (0.12 mmol), 2-substituted indole derivatives (0.1 mmol), K2CO3 (0.15 mmol), TEBA (0.12 mmol) and 10 mL CH3CN was added in a round bottom flask, and the mixture was stirred at room temperature for 6 h. The reaction was monitored by TLC. Then 30 mL of acetic ether was added into the reaction mixture, the products were filtered. The filtrate was concentrated in vacuo to give blue solid. The blue residue was purified by flash chromatography on silica gel using acetic ether and petroleum ether as eluate.
  • 32
  • [ 55577-25-8 ]
  • [ 1402597-35-6 ]
  • 33
  • [ 55577-25-8 ]
  • 2-<i>m</i>-toluidino-1-<i>p</i>-tolyl-ethanone [ No CAS ]
  • [ 1401073-71-9 ]
  • 34
  • [ 55577-25-8 ]
  • [ 7188-38-7 ]
  • [ 938374-55-1 ]
  • 35
  • [ 1449517-04-7 ]
  • [ 55577-25-8 ]
 

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Technical Information

Categories

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[ 55577-25-8 ]

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