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Chemical Structure| 35490-77-8 Chemical Structure| 35490-77-8

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Chemical Structure| 35490-77-8

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Product Details of [ 35490-77-8 ]

CAS No. :35490-77-8
Formula : C9H10N2
M.W : 146.19
SMILES Code : N#CC1=C(C)C=C(C)C=C1N
MDL No. :MFCD04222137
InChI Key :UMSQQTROMHEPSS-UHFFFAOYSA-N
Pubchem ID :12448667

Safety of [ 35490-77-8 ]

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

Application In Synthesis of [ 35490-77-8 ]

* 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 [ 35490-77-8 ]

[ 35490-77-8 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 69245-70-1 ]
  • [ 35490-77-8 ]
  • 2
  • [ 58579-99-0 ]
  • [ 35490-77-8 ]
  • 3
  • [ 35490-77-8 ]
  • [ 56396-59-9 ]
  • 4
  • [ 35490-77-8 ]
  • sodium dicyano-cuprate [ No CAS ]
  • [ 404834-11-3 ]
  • 5
  • [ 35490-77-8 ]
  • (1S,5S)-7-Ethyl-bicyclo[3.3.1]non-6-en-3-one [ No CAS ]
  • rac-12-amino-9-ethyl-6,7,10,11-tetrahydro-1,3-dimethyl-7,11-methanocycloocta[b]quinoline [ No CAS ]
  • 6
  • [ 1635-84-3 ]
  • [ 35490-77-8 ]
  • 7
  • [ 32315-10-9 ]
  • [ 35490-77-8 ]
  • [ 1392213-81-8 ]
  • 8
  • [ 99-12-7 ]
  • [ 105-34-0 ]
  • [ 35490-77-8 ]
YieldReaction ConditionsOperation in experiment
54% With potassium cyanide; water; potassium hydroxide; In N,N-dimethyl-formamide; at 60℃;Inert atmosphere; 1,3-dimethyl-5-nitrobenzene (117.9 g, 780 mmol) in a round bottom flask immersed in water under a stream of nitrogen,Methyl cyanoacetate (231.8 g, 2339 mmol),Potassium cyanide (55.9g, 858mmol) and potassium hydroxide (87.5g, 1560mmol) were added and stirred.960 mL of dimethylformamide was added, the temperature was raised to 60C, and the mixture was stirred overnight.The next day, the change in TLC was checked and the temperature of the flask was set to room temperature. The reaction solution was concentrated under reduced pressure to remove all possible dimethylformamide.The concentrate was transferred to a reactor with a small amount of dichloromethane, and 500 mL of a 10% aqueous sodium hydroxide solution was added thereto, followed by stirring.After reflux stirring for about 1 hour, the temperature was brought to room temperature. Extracted with ethyl acetate and water.It was separated by column chromatography using ethyl acetate and heptane. 61.6 g of [Intermediate 11-a] was obtained by recrystallization from toluene and heptane. (Yield 54%)
54% With potassium cyanide; potassium hydroxide; In water; N,N-dimethyl-formamide; at 60℃;Inert atmosphere; Under a stream of nitrogen, 1,3-dimethyl-5-nitrobenzene (117.9 g, 780 mmol), methyl cyanoacetate (231.8 g, 2339 mmol), potassium cyanide (55.9 g, 858 mmol), potassium hydroxide in a round bottom flask submerged in water (87.5 g, 1560 mmol) was added and stirred. 960 mL of dimethylformamide was added and the temperature was raised to 60 C., followed by stirring overnight. The next day, the change in TLC was confirmed and the temperature of the flask was brought to room temperature. The reaction solution was concentrated under reduced pressure to remove all possible dimethylformamide. The concentrate was transferred to the reactor with a small amount of dichloromethane and 500 mL of a 10% aqueous sodium hydroxide solution was added and stirred. After reflux stirring for about 1 hour, the temperature was set to room temperature. It was extracted with ethyl acetate and water. Column chromatography was performed using ethyl acetate and heptane. Recrystallization with toluene and heptane gave [Intermediate 13-a] 61.6 g. (Yield 54%)
  • 9
  • potassium cyanide [ No CAS ]
  • [ 99-12-7 ]
  • [ 105-34-0 ]
  • [ 35490-77-8 ]
YieldReaction ConditionsOperation in experiment
54% With potassium hydroxide; In water; N,N-dimethyl-formamide; at 60℃;Inert atmosphere; 1,3-dimethyl-5-nitrobenzene (117.9 g, 780 mmol), methyl cyanoacetate (231.8 g, 2339 mmol), potassium cyanide (55.9 g, 858 mmol), potassium hydroxide in a round bottom flask immersed in water under a stream of nitrogen (87.5g, 1560mmol) was added and stirred. 960 mL of dimethylformamide was added, the temperature was raised to 60C, and the mixture was stirred overnight. The next day, the change in TLC was checked and the temperature of the flask was set to room temperature. The reaction solution was concentrated under reduced pressure to remove all possible dimethylformamide. The concentrate was transferred to a reactor with a small amount of dichloromethane, and 500 mL of a 10% aqueous sodium hydroxide solution was added thereto, followed by stirring. After reflux stirring for about 1 hour, the temperature was brought to room temperature. Extracted with ethyl acetate and water. It was separated by column chromatography using ethyl acetate and heptane. 61.6 g of [Intermediate 21-a] was obtained by recrystallization from toluene and heptane. (Yield 54%)
 

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