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[ CAS No. 236750-65-5 ]

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Chemical Structure| 236750-65-5
Chemical Structure| 236750-65-5
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CAS No. :236750-65-5 MDL No. :MFCD17676647
Formula : C13H16N2O6 Boiling Point : 459.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :296.28 g/mol Pubchem ID :16063393
Synonyms :

Safety of [ 236750-65-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 236750-65-5 ]

  • Upstream synthesis route of [ 236750-65-5 ]
  • Downstream synthetic route of [ 236750-65-5 ]

[ 236750-65-5 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 236750-65-5 ]
  • [ 64-18-6 ]
  • [ 179688-29-0 ]
Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
  • 2
  • [ 236750-65-5 ]
  • [ 179688-29-0 ]
Reference: [1] Patent: CN104945332, 2017, B,
[2] Patent: CN107445907, 2017, A,
  • 3
  • [ 80407-68-7 ]
  • [ 236750-65-5 ]
YieldReaction ConditionsOperation in experiment
92.33% at 70℃; for 0.0166667 h; Example 17. Example 2 was repeated except that the nitration reaction temperature was 70 °C.
1) Nitrification reaction: 200 g of raw material is dissolved in 3 L of glacial acetic acid to dissolve as material I, concentrated sulfuric acid is used as material II, and concentrated nitric acid is used as material III.Adjust the flow rate of the flow pump so that the flow rate of the material I is 20 ml/min, and the flow rate of the material II is 10 ml/min.The flow rate of the material III is 6 ml/min, the molar ratio of the raw material to the HNO3 is 1:1.5, and the mass ratio of the concentrated nitric acid to the concentrated sulfuric acid is 1:4.The reaction temperature is 60 ° C, the residence time of the reaction is 60 seconds, and the temperature of the cooling module is 20 ° C.Collecting the reaction liquid flowing out from the outlet of the cooling module for post-treatment, which means that glacial acetic acid is recovered by distillation under reduced pressure.The residue was added to 1.2 L of water and extracted twice with 1 L of ethyl acetate.The organic phase is washed with a saturated sodium hydrogencarbonate solvent until neutral, dried over anhydrous sodium sulfate, and then evaporated.The nitrated product was obtained in 215.21 g, the yield was 90.58percent, and the purity was 98.95percent.
90% at 40℃; for 2 h; c) 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile:; To 70percent nitric acid (84ml) maintained at 4O0C was added 3,4-bis(2- methoxyethoxy) benzonitrile (42g) of the formula V slowly over a period of 2 hours under stirring. After complete addition of the compound, stirring continued for further an hour, quenched the reaction mass in ice-water, filtered, washed the precipitate with water and dried the material at 500C to get yellow solid i.e. 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile of the formula Vl (44.5g, 90percent); m.p. 139-143°C.NMR (CDCI3): δ 3.45 (s, 6H), 3.82(m, 4HO, 4.30(m, 4H), 7.28(s, 1H) and 7.85(s, 1 H).
90% at 40℃; for 3 h; c) 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile:; To 70percent nitric acid (84ml) maintained at 4O0C was added 3,4-bis(2- methoxyethoxy) benzonitrile (42g) of the formula V slowly over a period of 2 hours under stirring. After complete addition of the compound, stirring continued for further an hour, quenched the reaction mass in ice-water, filtered, washed the precipitate with water and dried the material at 500C to get yellow solid i.e. 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile of the formula Vl (44.5g, 90percent); m.p. 139-143°C.NMR (CDCI3): δ 3.45 (s, 6H), 3.82(m, 4HO, 4.30(m, 4H), 7.28(s, 1H) and 7.85(s, 1 H).
47% at 20 - 50℃; for 48 h; Nitric acid (65 percent, 16.2 g, 254.5 mmol) was dropwise added directly into flask containing 3,4-bis(2-methoxyethoxy)benzonitrile (12.8 g, 50.9 mmol). The mixture was then heated with stirring to 50 °C until starting material was completely dissolved. After stirring for two days at RT the reaction mixture was dissolved with water (50 ml) and formed precipitate was filtered off and washed with water (100 ml). After crystallization from chloroform the title compound was obtained in form of white crystals (7.1 g, 47 percent). Spectral data were in agreement with literature.Chandregowda, Venkateshappa; Rao, Gudapati Ventakeswara; Reddy, Goukanapalli Chandrasekara Heterocycles, 2007 , vol. 71, 1 p. 39 - 48.
47% at 20 - 50℃; Nitric acid (65 percent, 16.2 g, 254.5 mmol) was dropwise added directly into flask containing 3,4- bis(2-methoxyethoxy)benzonitrile (12.8 g, 50.9 mmol). The mixture was then heated with stirring to 50 °C until starting material was completely dissolved. After stirring for two days at RT the reaction mixture was dissolved with water (50 ml) and formed precipitate was filtered off and washed with water (100 ml). After crystallization from chloroform the title compound was obtained in form of white crystals (7.1 g, 47 percent). Spectral data were in agreement with literature. Chandregowda, Venkateshappa; Rao, Gudapati Ventakeswara; Reddy, Goukanapalli Chandrasekara Heterocycles, 2007 , vol. 71 , 1 p. 39 - 48.

Reference: [1] Patent: CN108358798, 2018, A, . Location in patent: Paragraph 0055; 0065; 0075; 0085; 0094-0099; 0102
[2] Patent: WO2007/138612, 2007, A2, . Location in patent: Page/Page column 10
[3] Patent: WO2007/138613, 2007, A2, . Location in patent: Page/Page column 11-12
[4] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 3, p. 909 - 914
[5] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
[6] Patent: EP2769723, 2014, A1, . Location in patent: Paragraph 0150-0151
[7] Patent: WO2014/128206, 2014, A1, . Location in patent: Page/Page column 48-49
[8] Patent: CN106957274, 2017, A, . Location in patent: Paragraph 0051-0054
[9] Patent: CN107445907, 2017, A, . Location in patent: Paragraph 0062; 0063; 0064; 0065
  • 4
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Reference: [1] Patent: EP2769723, 2014, A1,
[2] Patent: WO2014/128206, 2014, A1,
[3] Patent: CN106957274, 2017, A,
  • 5
  • [ 80407-64-3 ]
  • [ 236750-65-5 ]
Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
[2] Patent: CN107445907, 2017, A,
  • 6
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Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
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  • [ 139-85-5 ]
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Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
  • 8
  • [ 1418289-91-4 ]
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Reference: [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 3, p. 909 - 914
  • 9
  • [ 819813-71-3 ]
  • [ 236750-65-5 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 3, p. 909 - 914
  • 10
  • [ 99-50-3 ]
  • [ 236750-65-5 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 3, p. 909 - 914
  • 11
  • [ 121-33-5 ]
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Reference: [1] Patent: CN106957274, 2017, A,
  • 12
  • [ 4421-08-3 ]
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Reference: [1] Patent: CN106957274, 2017, A,
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YieldReaction ConditionsOperation in experiment
90.42% With palladium 10% on activated carbon; hydrogen In methanol at 90℃; for 0.00833333 h; Example 30. Example 1 was repeated, which differs from Example 1 in that the nitration product has a catalytic reaction residence time of 30 s.
2) catalytic hydrogenation reaction: 200 g of the nitrification product obtained in the previous step is dissolved in 5 L of anhydrous methanol,Subsequently, 10 g of a Pd/C catalyst having a Pd content of 10percent is added, and the mixture is stirred and mixed to form a material IV.H2 is used as material V, and the flow rate of the slurry pump is adjusted so that the flow rate of the material IV is 40.0 g/min, and the flow rate of the gas flow meter is adjusted to 700 ml/min.The molar ratio of nitro compound to H2 is 1:3.5, the reaction temperature is 90 ° C, the temperature of the cooling module is 25 ° C, and the residence time of the reaction is 25 s.The reaction pressure is 1.5 MPa, and the reaction liquid flowing out from the outlet of the cooling module is collected for post-treatment.The post-treatment means that the catalyst Pd/C is recovered by filtration, the organic solvent is recovered by distillation under reduced pressure, and the residue is added with 1.2 L of acetone to stir the solvent.Add 450 ml of concentrated hydrochloric acid, stir and crystallize for 1 h, filter, and put the filter cake into 2 L of water.Add 2mol/L NaOH solution to adjust the pH of the system to about 8.0, and add 2L of ethyl acetate to extract twice.Add 1 L of ethyl acetate each time and combine the organic phases.After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to give an amine product of 160.83 g,yield: 8.077percent, purity 99.43percent.
Reference: [1] Organic Process Research and Development, 2007, vol. 11, # 5, p. 813 - 816
[2] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 3, p. 909 - 914
[3] Patent: CN108358798, 2018, A, . Location in patent: Paragraph 0052; 0057; 0067; 0077; 0087; 0112-0119; 0123
[4] Patent: WO2007/138612, 2007, A2, . Location in patent: Page/Page column 10-11
[5] Patent: WO2007/138613, 2007, A2, . Location in patent: Page/Page column 10-11
[6] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 689 - 697
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