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Chemical Structure| 25978-74-9 Chemical Structure| 25978-74-9

Structure of 25978-74-9

Chemical Structure| 25978-74-9

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Product Details of [ 25978-74-9 ]

CAS No. :25978-74-9
Formula : C10H9NO3
M.W : 191.18
SMILES Code : O=C(OC)C1=CC=C(OC)C(C#N)=C1
MDL No. :MFCD00052930
InChI Key :RYJSFYBJYKFNCF-UHFFFAOYSA-N
Pubchem ID :2801011

Safety of [ 25978-74-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H331
Precautionary Statements:P261-P311
Class:6.1
UN#:3439
Packing Group:

Application In Synthesis of [ 25978-74-9 ]

* 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.

  • Upstream synthesis route of [ 25978-74-9 ]

[ 25978-74-9 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 35450-37-4 ]
  • [ 25978-74-9 ]
YieldReaction ConditionsOperation in experiment
79% With copper(l) cyanide In N,N-dimethyl-formamide at 140℃; for 6 h; To a solution of compound y (1.1 g, 4.4 mol) in dimethylformamide (10 mL) was added cuprous cyanide (1.2 g, 13.2 mmol). And the mixture was heated to 140 ° C for 6 hours. The reaction system was cooled and then ethyl acetate (25 mL) was added. The extracted organic phase was washed with saturated brine and the concentrated residue was dried and concentrated by flash column chromatography (petroleum ether: ethyl acetate = 10: 1) to give a white solid Compound z: Methyl 3-cyano-4-methoxybenzoate (662 mg, yield 79percent).
References: [1] Patent: CN106146504, 2016, A, . Location in patent: Paragraph 0219; 0220; 0221; 0224; 0225.
  • 2
  • [ 156001-68-2 ]
  • [ 74-88-4 ]
  • [ 25978-74-9 ]
YieldReaction ConditionsOperation in experiment
52% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2 h; Inert atmosphere To a stirred solution of methyl 3-cyano-4-hydroxybenzoate (2.0 g, 1 1.20 mmol) in DMF (20 mL) were added CH3I (2.40 g, 16.01 mmol) and K2CO3 (2.30 g, 16.01 mmol) at 0 0C under a N2 atmosphere. The reaction mixture was stirred at 80 0C for 2 h. After completion of starting material (monitored by TLC), reaction mixture was diluted with water and extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with water (2 x 50 mL), brine and dried over anhydrous Na24. After filtration and evaporation in vacuo, the crude material was purified by silica gel column chromatography to afford methyl 3-cyano-4-methoxybenzoate (1.1 g, 52percent), as a pale yellow solid.
References: [1] Patent: WO2009/158393, 2009, A1, . Location in patent: Page/Page column 109.
  • 3
  • [ 35450-37-4 ]
  • [ 25978-74-9 ]
YieldReaction ConditionsOperation in experiment
79% at 140℃; for 6 h; To a solution of Compound d' (1.1 g, 4.4 mol) dissolved in dimethyl formamide (10 mL), cuprous cyanide (1.2 g, 13.22 mmol) was added, heated to 140°C, and stirred for 6 hrs. The reaction system was cooled, added with ethyl acetate (25 mL), and extracted. Then, the organic phase was washed with saturated saline, dried and concentrated. The resulting residue was separated by flash column chromatography (petroleum ether:ethyl acetate=10:1), to obtain Compound e': methyl 3-cyano-4-methoxybenzoate as a white solid (662 mg, yield 79percent).
References: [1] Patent: EP3284743, 2018, A1, . Location in patent: Paragraph 0155.
[2] Journal of Materials Chemistry C, 2016, vol. 4, # 19, p. 4269 - 4277.
  • 4
  • [ 77-78-1 ]
  • [ 156001-68-2 ]
  • [ 25978-74-9 ]
References: [1] Patent: US2012/184587, 2012, A1, . Location in patent: Page/Page column 33.
  • 5
  • [ 156001-68-2 ]
  • [ 25978-74-9 ]
References: [1] Patent: US5939439, 1999, A, .
  • 6
  • [ 99-76-3 ]
  • [ 25978-74-9 ]
References: [1] Journal of Materials Chemistry C, 2016, vol. 4, # 19, p. 4269 - 4277.
[2] Patent: US2012/184587, 2012, A1, .
[3] Patent: WO2009/158393, 2009, A1, .
  • 7
  • [ 121-98-2 ]
  • [ 25978-74-9 ]
References: [1] Journal of Materials Chemistry C, 2016, vol. 4, # 19, p. 4269 - 4277.
[2] Patent: CN106146504, 2016, A, .
[3] Patent: EP3284743, 2018, A1, .
  • 8
  • [ 29415-97-2 ]
  • [ 25978-74-9 ]
References: [1] Patent: US2012/184587, 2012, A1, .
[2] Patent: WO2009/158393, 2009, A1, .
 

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