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Chemical Structure| 1125-60-6 Chemical Structure| 1125-60-6
Chemical Structure| 1125-60-6

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CAS No.: 1125-60-6

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Product Details of [ 1125-60-6 ]

CAS No. :1125-60-6
Formula : C9H8N2
M.W : 144.17
SMILES Code : NC1=CC=CC2=C1C=CN=C2
MDL No. :MFCD00006907
InChI Key :DTVYNUOOZIKEEX-UHFFFAOYSA-N
Pubchem ID :70766

Safety of [ 1125-60-6 ]

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

Application In Synthesis [ 1125-60-6 ]

* 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 [ 1125-60-6 ]

[ 1125-60-6 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 1125-60-6 ]
  • [ 5430-45-5 ]
  • 2
  • [ 1125-60-6 ]
  • [ 201150-73-4 ]
  • 3
  • [ 1125-60-6 ]
  • [ 107819-90-9 ]
  • [ 883876-30-0 ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine;mercury dichloride; In dichloromethane; at 20℃; for 15h; To a solution of Isoquinolin-5-amine (1.11 g, 7.69 mmol, Aldrich) and <strong>[107819-90-9]1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea</strong> (2.28 g, 7.85 mmol, Aldrich) in DCM (25 mL) was added triethylamine (1.60 g, 15.78 mmol, Aldrich) and mercuric chloride (2.1 g, 7.74 mmol, Aldrich). The reaction mixture was stirred at room temperature for 15 h and filtered. The filter cake was washed with DCM (2*25 mL). The combined filtrates were concentrated and the residue was purified by silica gel column chromatography, eluding with EtOAc/hexane (1:5) to give 2.29 mg (77percent) of the title compound as a pale-yellow amorphous solid. MS (ESI, pos. ion) m/z: 387 (M+1).
  • 4
  • [ 1125-60-6 ]
  • [ 27655-41-0 ]
YieldReaction ConditionsOperation in experiment
56% With sodium hydrogencarbonate; sodium nitrite; In hydrogenchloride; water; ethyl acetate; toluene; A. 5-Cyanoisoquinoline To a cold (0 C.) solution of 10.0 g (61.4 mmol) of 5-aminoisoquinoline in 288 mL of 1.5N hydrochloric acid, was added 15 mL of 5.2M sodium nitrite in water. After approximately 5 minutes, a cool saturated solution of sodium bicarbonate was added to the reaction mixture until the reaction solution tested negative using the iodide and start paper test. The resultant solution was poured into a cold (0-5 C.) biphasic mixture containing 300 ml of toluene and 150 mL of an aqueous solution containing 8.4 g (177 mmol) of sodium cyanide and 7.6 g (85 mmol) of copper cyanide. The resultant reaction mixture was warmed to room temperature, reacted for approximately 1 hour, and then diluted with a mixture of ethyl acetate and water. The resulting layers were separated, and the organic phase was dried over sodium sulfate, filtered, and then reduced to dryness under reduced pressure to provide 5.9 g of a yellow solid. Yield: 56%. 1 H NMR (CDCl3): δ 9.38 (s, 1H), 8.76 (d, J=5.89 Hz, 1H), 8.25 (d, J=8.29 Hz, 1H), 8.13 (d, J=8.30 Hz, 1H), 8.03 (d, J=8.59 Hz, 1H), 7.71 (t, J=7.78 Hz, 1H); IR (KBr): 3433, 3090, 3026, 2924, 2226, 1618, 1574, 1495, 1433, 1373, 1277, 1225, 1034, 829, 766, 714.
56% With sodium hydrogencarbonate; sodium nitrite; In hydrogenchloride; water; ethyl acetate; toluene; A. 5-Cyanoisoquinoline To a cold (0 C.) solution of 10.0 g (61.4 mmol) of 5-aminoisoquinoline in 288 mL of 1.5N hydrochloric acid, was added 15 mL of 5.2M sodium nitrite in water. After approximately 5 minutes, a cool saturated solution of sodium bicarbonate was added to the reaction mixture until the reaction solution tested negative using the iodide and starch paper test. The resultant solution was poured into a cold (0-5 C.) biphasic mixture containing 300 ml of toluene and 150 mL of an aqueous solution containing 8.4 g (177 mmol) of sodium cyanide and 7.6 g (85 mmol) of copper cyanide. The resultant reaction mixture was warmed to room temperature, reacted for approximately 1 hour, and then diluted with a mixture of ethyl acetate and water. The resulting layers were separated, and the organic phase was dried over sodium sulfate, filtered, and then reduced to dryness under reduced pressure to provide 5.9 g of a yellow solid. Yield: 56%. 1 H NMR (CDCl3): δ9.38 (s, 1H), 8.76 (d, J=5.89 Hz, 1H), 8.25 (d, J=8.29 Hz, 1H), 8.13 (d, J=8.30 Hz, 1H), 8.03 (d, J=8.59 Hz, 1H), 7.71 (t, J=7.78 Hz, 1H); IR (KBr): 3433, 3090, 3026, 2924, 2226, 1618, 1574, 1495, 1433, 1373, 1277, 1225, 1034, 829, 766, 714.
  • 5
  • [ 1125-60-6 ]
  • [ 50607-30-2 ]
  • [ 1052689-39-0 ]
YieldReaction ConditionsOperation in experiment
67% In ethanol; for 3 - 4h;Heating / reflux; lsoquinolin-5-ylamine (4 g, 27.9 mmol) and <strong>[50607-30-2]piperidine-2,4-dione</strong> (4.1 g, 36.2 mmol) were heated at reflux in absolute ethanol (200 ml.) with a Dean-Stark apparatus for 3-4 hours. The solvent was concentrated under vacuum and the resulting solid <n="25"/>foam, corresponding to the title compound, was dried under vacuum and used in the next step without further purification (4.45 g, yield 67percent).1 H NMR (400 MHz, CD3OD) delta ppm 2.76 (t, J=7.95, 2 H) 3.48 (t, J=8.01 , 2 H) 4.58 (s, 1H) 7.73 (m, 2H) 7.89 (d, J=7.89, 1 H) 8.03 (m, 1 H) 8.48 (d, J=8.04, 1 H) 9.28 (s, 1 H). [M+H]+= 240
  • 6
  • [ 1125-60-6 ]
  • [ 628-36-4 ]
  • 5-(4H-1,2,4-triazol-4-yl)isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
39.7% With triethylamine; In pyridine; at 100℃; for 4h;Sealed tube; 247A. 5-(4H-l,2,4-Triazol-4-yl)isoquinoline: Using a modified procedure described by Varano (Varano, F. et al, J. Med. Chem., 45(5): 1035-1044 (2002)). To two large microwave vials containing in equal portions a suspension of isoquinolin-5-amine (0.865 g, 6.0 mmol) and <strong>[628-36-4]N'-formylformohydrazide</strong> (0.793 g, 9 mmol) in pyridine (24 mL) was added, TMSI (5.71 mL, 45 mmol) dropwise followed by TEA (2.84 mL, 20.4 mmol). The reaction vessels were sealed and heated at 100 °C for 4 h. The reaction was cooled to room temperature, concentrated, the residue dissolved in EtOAc, washed with 1.5M potassium phosphate, brine, dried over sodium sulfate, filtered, and concentrated. The crude residue was purified by normal phase column chromatography to give a solid (0.467g, 39.7percent yield). NMR (400MHz, DMSO-d6) delta 9.45 (d, J = 0.7 Hz, 1H), 8.95 (s, 2H), 8.56 (d, J = 6.2 Hz, 1H), 8.35 - 8.30 (m, 1H), 7.93 (dd, J = 7.5, 1.1 Hz, 1H), 7.80 (dd, J = 8.1, 7.5 Hz, 1H), 7.29 (d, J = 6.2 Hz, 1H). MS (ESI) m/z: 197 (M+H)+.
 

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