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Chemical Structure| 1891-19-6 Chemical Structure| 1891-19-6

Structure of 1891-19-6

Chemical Structure| 1891-19-6

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Product Details of [ 1891-19-6 ]

CAS No. :1891-19-6
Formula : C12H8N2O
M.W : 196.20
SMILES Code : [O-][N+]1=C2C3=NC=CC=C3C=CC2=CC=C1
MDL No. :MFCD22055248

Safety of [ 1891-19-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 1891-19-6 ]

* 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 [ 1891-19-6 ]

[ 1891-19-6 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1891-19-6 ]
  • [ 151-50-8 ]
  • [ 1082-19-5 ]
YieldReaction ConditionsOperation in experiment
24.0% With benzoyl chloride; In water; at 20℃; Step 2; 23 g [1,10]phenanthroline-N-oxide and 37.5 g KCN were dissolved in 2.5 L water to form a mixture, and 65 g benzoyl chloride was added into the mixture drop by drop. Then, the mixture was stirred at room temperature overnight. After completion of reaction, solids were collected, purified by silica gel column (Hexane/CH2Cl2=1/2) and dried to obtain solids [1,10]phenanthroline-2-carbonitrile 6 g (yield 24.0%).
  • 2
  • [ 1891-19-6 ]
  • [ 7089-68-1 ]
YieldReaction ConditionsOperation in experiment
57% With N,N-dimethyl-formamide; trichlorophosphate; In dichloromethane; at 0 - 25℃;Inert atmosphere; General procedure: The procedure is identical to general procedure I, except that reactions were conducted at 0.2 M concentration with N-oxide (1.00 equiv), POBr3 (3.00 equiv), DMF (1.50 equiv) at rt. 4.2 General procedure I for the bromination of azine N-oxides (0013) To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1 M) at 0 C is added POBr3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7-8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.
48% With sodium chloride; trichlorophosphate; In N,N-dimethyl-formamide; at 100℃; for 6h; 1,10-phenanthroline-N-oxide (1.96 g, 10 mmol), NaCl (11.7 g, 0.2 mol) was added to DMF (40 mL). Slowly add POCl3 (30 mmol) to the solution. The reaction solution was heated at 100 C for 6 h and allowed to cool to room temperature. Ammonia water (50 mL) was added to the reaction mixture, and extracted with chloroform. The organic phase was collected, dried over anhydrous sodium sulfate and filtered. The organic phase was removed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography to give 2-chloro-1,10-phenanthroline 1.03 g (4.8 mmol, 48.0%).
44% With sodium chloride; trichlorophosphate; In N,N-dimethyl-formamide; at 0 - 100℃; for 6h;Inert atmosphere; Schlenk technique; Sealed tube; To the mixture of 1,10-phenanthroline-N-oxide (196.1 mg, 1 mmol, 1.0 eq.),sodium chloride in anhydrous DMF, a neat POCl3 (3 mmol, 3.0 eq.) was added slowly after cooling to 0 C. Then, the mixture was heated to 100 C for 6 hours. After cooling to room temperature, water was added, and the mixture was quenched with saturated ammonium chloride (aqueous) and saturated with NaCl (20 mmol, 20.0 eq.), solids were filtered, and the solution was extracted with chloroform.The combined extracts were washed with brine, dried over MgSO4, and evaporated, and then purified by column chromatography using eluent EA/PE (3:2) to get the target product as a light yellow solid, (94.2 mg, 0.44 mmol, yield = 44%). The spectral data were in accordance with the literature [55]. 1H-NMR(400MHz, CDCl3) 9.12 (dd, J = 1.7, 4.1 Hz, 1H), 8.57 (d, J = 9.4 Hz, 1H), 8.53 (dd, J = 1.7, 8.0 Hz, 1H),8.07-8.03 (m, 2H), 7.84 (d, J = 8.4 Hz, 1H), 7.81 (dd, J = 4.3, 8.2 Hz, 1H); 13C-NMR (400MHz, CDCl3) 151.3, 150.7, 146.0, 145.0, 138.7, 136.0, 129.0, 127.2, 126.9, 125.7, 124.2, 123.4.
  • 3
  • potassium cyanide [ No CAS ]
  • [ 1891-19-6 ]
  • [ 1082-19-5 ]
YieldReaction ConditionsOperation in experiment
79% With benzoyl chloride; In water; at 20℃; To a solution of 10 g(51 mmol) of 1,10-phenanthroline-1-oxide and 10 g(154 mmol) of potassium cyanide dissolved in 80 mL ofwater were added dropwise 10 mL (86 mmol) of benzoylchloride under magnetic stirring (total addition required15 min). A brown solid precipitated. The disappearanceof 1,10-phenanthroline-1-oxide and the appearance of 2-cyano-1,10-phenanthroline were followed by TLC with dichloromethane/methanol (98/2v/v) as eluent. The reaction was stopped when complete disappearance of 1,10-phenanthroline-1-oxide was achieved (ca. 2 h). The precipitate was collected by suction filtration,washed 4 times with water and 5% sodium hydroxide solution alternatively in order toremove the byproducts of benzoyl chloride and dried over vacuum to yield a brown solid(8.3 g, 79% yield). The product was engaged in the next step without further purification.
  • 4
  • [ 1891-19-6 ]
  • [ 7677-24-9 ]
  • [ 1082-19-5 ]
YieldReaction ConditionsOperation in experiment
45 g With magnesium sulfate; benzoyl chloride; In dichloromethane; at 25℃; for 72h;Cooling with ice; First, the step 50g of the obtained yellow solid powder wasdissolved in 300mL dried over anhydrous magnesium sulfate and the methylenechloride, transferred to a 2L three bottles and stirred, ice-water bath wascooled to below 10 C. Was added dropwise trimethylsilyl cyanide (TMSCN,200mL), maintaining the internal temperature less than 25 C. After theaddition was complete, the ice water bath for half an hour. Benzoyl chloride(60mL)Maintain the internal temperature less than 25 C. Afterthe addition, the reaction at room temperature for 72 hours. Ice-salt bathcooling, the internal temperature drops below 0 C. Dropwise addition ofsaturated sodium bicarbonate solution (lmL), maintaining the internaltemperature less than 10 C, after the addition was complete the reaction wasstirred for 1 hour at room temperature. The reaction system was then charged toa separatory funnel 5L was added dichloromethane (2000mL). The organic layerwas washed with water (1000mLX3), then with saturated brine (1000mLX2), driedover anhydrous sodium sulfate. The desiccant was filtered off. Pressureconcentrated and dried to giveTo a yellow semi-solid was stirred with 500mL of petroleumether washed 4 hours. Filtered, the filter cake was washed with petroleum ether(100mL). Wet product was dried in vacuo 40 C for 8 hours to obtain a yellowsolid 35~45g powder (Compound 3).
With benzoyl chloride; In dichloromethane; at 10 - 25℃;Cooling with ice; The first step on the obtained yellow solid powder was dissolved in 40g 300mL dried over anhydrous magnesium sulfate and methylene chloride, transferred 2L three-necked flask and stirred, ice-water bath was cooled to less 10 .Was added dropwise trimethylsilyl cyanide (TMSCN, 200mL), maintaining the internal temperature less than 25 deg.] C. After the addition was complete, the ice water bath for half an hour.Benzoyl chloride (60mL), maintaining the internal temperature less than 25 .After the addition, the reaction at room temperature for 72 hours.Ice-salt bath to cool the internal temperature drops below 0 .Dropwise addition of saturated sodium bicarbonate solution (1000mL), keeping the internal temperature less than 10 , after the addition was complete the reaction was stirred for 1 hour at room temperature.The reaction system was then charged to a separatory funnel 5L was added dichloromethane (2000mL).The organic layer was washed with water (1000mLX3), then with saturated brine (1000mLX2), dried over anhydrous sodium sulfate.The desiccant was filtered off.Pressurized concentrated to dryness to give a yellow semi-solid was stirred with 500mL of petroleum ether and washed 4 hours.Filtered, the filter cake was washed with petroleum ether (100mL).40 wet product was dried under vacuum for 8 hours to obtain a yellow solid powder 35 ~ 45g (Compound 21).
 

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