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Chemistry
Organic Building Blocks
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5-Chloro-2,3-dimethoxybenzaldehyde
Chemistry
Organic Building Blocks
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Chlorides Ethers Aldehydes Benzene Compounds Benzene Compounds

[ CAS No. 86232-28-2 ]

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3d Animation Molecule Structure of 86232-28-2
Chemical Structure| 86232-28-2
Chemical Structure| 86232-28-2
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Quality Control of [ 86232-28-2 ]

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Product Details of [ 86232-28-2 ]

CAS No. :86232-28-2 MDL No. :MFCD01743107
Formula : C9H9ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :200.62 g/mol Pubchem ID :-
Synonyms :

Safety of [ 86232-28-2 ]

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 [ 86232-28-2 ]

* 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 [ 86232-28-2 ]

[ 86232-28-2 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 86232-28-2 ]
  • [ 72517-22-7 ]
YieldReaction ConditionsOperation in experiment
77% With potassium permanganate In water for 5h; Heating;
14% With potassium permanganate In water; acetone at 20℃; for 22h;
Multi-step reaction with 2 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating
Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[2]Stark, Daniela; Piel, Markus; Huebner, Harald; Gmeiner, Peter; Gruender, Gerhard; Roesch, Frank [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 21, p. 6819 - 6829]
[3]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 2
  • [ 86232-28-2 ]
  • [ 86232-27-1 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; hydrazine hydrate 1) reflux, 2) reflux; Yield given. Multistep reaction;
Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 3
  • [ 86232-28-2 ]
  • [ 86232-35-1 ]
YieldReaction ConditionsOperation in experiment
82% With methanol; C25H29ClNO2Rh; caesium carbonate at 90℃; for 1h;
81% With sodium tetrahydroborate In isopropyl alcohol for 1h; Heating;
Reference： [1]Aboo, Ahmed H.; Bennett, Elliot L.; Deeprose, Mark; Robertson, Craig M.; Iggo, Jonathan A.; Xiao, Jianliang [Chemical Communications, 2018, vol. 54, # 83, p. 11805 - 11808]
[2]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 4
  • [ 86232-26-0 ]
  • [ 67-64-1 ]
  • [ 77-78-1 ]
  • [ 86232-28-2 ]
  • [ 86232-29-3 ]
YieldReaction ConditionsOperation in experiment
1: 75% 2: 11% With potassium carbonate In acetone for 5h; Heating;
Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 5
  • [ 86232-26-0 ]
  • [ 77-78-1 ]
  • [ 86232-28-2 ]
  • [ 86232-29-3 ]
YieldReaction ConditionsOperation in experiment
1: 11% 2: 75% With potassium carbonate In acetone for 5h; Heating;
Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 6
  • [ 86232-28-2 ]
  • [ 74-88-4 ]
  • [ 117052-18-3 ]
YieldReaction ConditionsOperation in experiment
With magnesium 2.) ether, benzene, reflux, 6 h; Yield given. Multistep reaction;
Reference： [1]Kuleshyus, V. A.; Gaidyalis, P. G.; Pyatrauskas, O. Yu.; Daukshas, V. K. [Pharmaceutical Chemistry Journal, 1988, vol. 22, # 7, p. 551 - 553][Khimiko-Farmatsevticheskii Zhurnal, 1988, vol. 22, # 7, p. 827 - 830]
YieldReaction ConditionsOperation in experiment
5-Chlor-2-hydroxy-3-methoxy-benzaldehyd, Dimethylsulfat/wss. NaOH, 50grad;
  • 8
  • [ 7740-05-8 ]
  • [ 86232-28-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 5 h, 2) reflux, 5 h 2: 75 percent / K2CO3 / acetone / 5 h / Heating
Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 9
  • [ 86232-28-2 ]
  • [ 87964-82-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating
Multi-step reaction with 3 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating
Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[2]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 10
  • [ 86232-28-2 ]
  • [ 86232-33-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating
Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 11
  • [ 86232-28-2 ]
  • [ 86232-31-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation
Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 12
  • [ 86232-28-2 ]
  • [ 86232-37-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C
Multi-step reaction with 3 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C
Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[2]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 13
  • [ 86232-28-2 ]
  • [ 86232-47-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 88 percent / AlBr3 / benzene / 3 h / Heating
Multi-step reaction with 6 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 88 percent / AlBr3 / benzene / 3 h / Heating
Multi-step reaction with 5 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating
Multi-step reaction with 5 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating

Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[2]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[3]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[4]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 14
  • [ 86232-28-2 ]
  • [ 86232-49-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane
Multi-step reaction with 7 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 88 percent / AlBr3 / benzene / 3 h / Heating 7: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane
Multi-step reaction with 6 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane
Multi-step reaction with 6 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane

Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[2]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[3]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[4]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 15
  • [ 86232-28-2 ]
  • [ 86232-41-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C
Multi-step reaction with 4 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C
Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[2]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 16
  • [ 86232-28-2 ]
  • [ 86232-39-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C
Multi-step reaction with 5 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C
Multi-step reaction with 4 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating
Multi-step reaction with 4 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating

Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[2]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[3]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[4]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 17
  • [ 86232-28-2 ]
  • [ 86232-52-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 95 percent / 20 h / Heating
Multi-step reaction with 7 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 88 percent / AlBr3 / benzene / 3 h / Heating 7: 95 percent / 20 h / Heating
Multi-step reaction with 6 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 95 percent / 20 h / Heating
Multi-step reaction with 6 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 95 percent / 20 h / Heating

Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[2]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[3]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[4]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 18
  • [ 86232-28-2 ]
  • [ 86232-43-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating
Multi-step reaction with 6 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating
Multi-step reaction with 5 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating
Multi-step reaction with 5 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating

Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[2]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[3]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[4]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 19
  • [ 86232-28-2 ]
  • [ 86232-45-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating 6: 74 percent / NH2OH / methanol / 6 h / Heating
Multi-step reaction with 7 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating 7: 74 percent / NH2OH / methanol / 6 h / Heating
Multi-step reaction with 6 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating 6: 74 percent / NH2OH / methanol / 6 h / Heating
Multi-step reaction with 6 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating 6: 74 percent / NH2OH / methanol / 6 h / Heating

Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[2]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[3]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[4]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 20
  • [ 86232-28-2 ]
  • [ 86232-50-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane 7: 85 percent / Heating
Multi-step reaction with 8 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 88 percent / AlBr3 / benzene / 3 h / Heating 7: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane 8: 85 percent / Heating
Multi-step reaction with 7 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane 7: 85 percent / Heating
Multi-step reaction with 7 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane 7: 85 percent / Heating

Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[2]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[3]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[4]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 21
  • [ 86232-28-2 ]
  • [ 86232-51-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 81 percent / 10percent aq. NaOH / 0.33 h
Multi-step reaction with 7 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 88 percent / AlBr3 / benzene / 3 h / Heating 7: 81 percent / 10percent aq. NaOH / 0.33 h
Multi-step reaction with 6 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 81 percent / 10percent aq. NaOH / 0.33 h
Multi-step reaction with 6 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 81 percent / 10percent aq. NaOH / 0.33 h

Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[2]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[3]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
[4]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 22
  • [ 148-53-8 ]
  • [ 86232-28-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 45 percent / chlorine / acetic acid / 5 h / 20 °C 2: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 5 h, 2) reflux, 5 h 3: 75 percent / K2CO3 / acetone / 5 h / Heating
Reference： [1]Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A.; Shtel'bene, V. P. [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528]
  • 23
  • [ 86232-28-2 ]
  • [ 117052-19-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) Mg / 2.) ether, benzene, reflux, 6 h 2: 85 percent / CrO3, pyridine / CH2Cl2 / 0.25 h
Reference： [1]Kuleshyus, V. A.; Gaidyalis, P. G.; Pyatrauskas, O. Yu.; Daukshas, V. K. [Pharmaceutical Chemistry Journal, 1988, vol. 22, # 7, p. 551 - 553][Khimiko-Farmatsevticheskii Zhurnal, 1988, vol. 22, # 7, p. 827 - 830]
  • 24
  • [ 86232-28-2 ]
  • [ 117052-23-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) Mg / 2.) ether, benzene, reflux, 6 h 2: 85 percent / CrO3, pyridine / CH2Cl2 / 0.25 h 3: 65 percent / aq. conc. HCl / ethanol / 10 h / Heating
Reference： [1]Kuleshyus, V. A.; Gaidyalis, P. G.; Pyatrauskas, O. Yu.; Daukshas, V. K. [Pharmaceutical Chemistry Journal, 1988, vol. 22, # 7, p. 551 - 553][Khimiko-Farmatsevticheskii Zhurnal, 1988, vol. 22, # 7, p. 827 - 830]
  • 25
  • [ 86232-28-2 ]
  • [ 75-16-1 ]
  • [ 117052-18-3 ]
YieldReaction ConditionsOperation in experiment
100% In diethyl ether at 20℃; for 4h; Reflux; 5 Example 5; The synthesis of ketone 3 was carried out by reducting the commercially available aldehyde 1 to the corresponding alcohol 2 following the procedure disclosed in WO06/081332A1, followed by the oxidation to ketone 3 with MnO2 with a good yield (Scheme 8).
96% Stage #1: 5-chloro-2,3-dimethoxybenzaldehyde; methylmagnesium bromide In diethyl ether; tert-butyl methyl ether at 9 - 33℃; Stage #2: With water; ammonium chloride In diethyl ether; tert-butyl methyl ether at 11 - 28℃; for 0.0833333h; 54 1 -(5 -Chloro-2,3 -dimethoxy-phenyl)-ethanol :; To a mixture of 5-chloro-2,3-dimethoxybenzaldehyde (339, 1.69 mol) in TBME (5.6 L) was added 3M methylmagnesium bromide in ether (660 mL, 1.98 mol) over 1 hour at 9 to 12 0C. The mixture was warmed at 33 0C for 1 hour 20 minutes. There was significant starting material present so more methylmagnesium bromide was added (590 mL, 1.77 mol) over 1 hour 20 minutes with the reaction temperature at 33 0C. The reaction was cooled to room temperature overnight and poured into ammonium chloride (20 wt %, 3 kg) over 5 minutes. The temperature rose from 11 to 28 0C. The reaction flask was rinsed with ammonium chloride solution (500 mL) and TBME (250 mL). The layers were separated and the organic layer was concentrated to an orange yellow thick oil. Yield: 348 g (96 % yield, 94 % purity).
75% Stage #1: 5-chloro-2,3-dimethoxybenzaldehyde; methylmagnesium bromide In diethyl ether at 0℃; for 3.5h; Heating / reflux; Stage #2: With water; ammonium chloride In diethyl ether at 0℃; 25 l-(5-Chloro-2,3-dimethoxy-phenyl)-ethanol:; To a stirred solution of 5-chloro-2,3-dimethoxy-benzaldehyde (7.Og, 34.90 mmol) in dry diethyl ether (500 mL) at 0 °C was added methylmagnesium bromide of 3.0 M in diethyl ether (29 mL, 87.22 mmol). The reaction mixture was brought to room temperature and stirred for 30 min; refluxed for 3 h; then cooled to 0 0C and quenched by adding saturated aqueous NH4Cl. The two liquid layers were separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water, dried, and concentrated to the crude compound which was purified by silica gel column (10-25 % ethyl acetate in hexanes) to afford l-(5-chloro-2,3-dimethoxy-phenyl)-ethanol (5.67 g, 75 %): 1H NMR (400 MHz, CDCl3): δ 7.00 (d, 1 H), 6.81 (d, 1 H), 5.11 (m, 1 H), 3.86 (s, 6 H), 2.30 (d, 1 H), 1.48 (d, 3 H). EPO
Reference： [1]Current Patent Assignee: Corporacion Quimico Farmaceutica Esteve SA - EP2103596, 2009, A1 Location in patent: Page/Page column 50
[2]Current Patent Assignee: GALENEA CORP - WO2006/81332, 2006, A1 Location in patent: Page/Page column 134
[3]Current Patent Assignee: GALENEA CORP - WO2006/81332, 2006, A1 Location in patent: Page/Page column 77
  • 26
  • [ 77-78-1 ]
  • [ 86232-28-2 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 5-chloro-2-hydroxy-3-methoxy-benzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 22 - 29℃; for 0.25h; Stage #2: dimethyl sulfate In N,N-dimethyl-formamide at 28 - 61℃; for 2h; 54 5-Chloro-2,3-dimethoxybenzaldehyde:; A mixture of 5-Chloro-2-hydroxy-3-methoxybenzaldehyde (275 g, 1.47 mol) and DMF were stirred as potassium carbonate (411 g, 2.97 mol) was added over 5 minutes. The mixture temperature rose from 22 to 29 0C over 10 minutes. Dimethylsulfate (283 g, 2.24 mol) was EPO added over 15 minutes causing a temperature rise from 28 to 47 0C. The mixture was then heated with a heating mantle to 61 0C over 15 minutes and stirred at 61 0C for 1.5 hours; the reaction was complete by TLC. The reaction mixture was cooled to 22 0C, transferred to a 22-L flask and diluted with water (8.2 L) over 5 minutes; the temperature rose to 38 0C. The light yellow mixture was filtered and the flask and filter cake rinsed with 1.5 L water. The solid was dried under vacuum for 15 hour at 50 0C. The material contained inorganic salts and was suspended in water (3 L) for 1.5 hours. After filtration and a 500 mL water rinse, the filter cake was dried under by suction and overnight at 65 0C under vacuum. Yield: 305 g (100 % yield, 99.1 % purity).
Reference： [1]Current Patent Assignee: GALENEA CORP - WO2006/81332, 2006, A1 Location in patent: Page/Page column 134-135
  • 27
  • [ 86232-28-2 ]
  • [ 865-47-4 ]
  • [ 623-70-1 ]
  • [ 116314-08-0 ]
YieldReaction ConditionsOperation in experiment
7.3 g (55%) In 1-methyl-pyrrolidin-2-one 32 5-(3,4-Dimethoxy-5-chlorophenyl)-2,4-pentadienoic acid EXAMPLE 32 5-(3,4-Dimethoxy-5-chlorophenyl)-2,4-pentadienoic acid To a solution containing 10.0 g of dimethoxy-5-chlorobenzaldehyde and 8.3 ml of ethyl crotonate in 65 ml of N-methylpyrrolidone 6.7 g of potassium tert.-butoxide was added with stirring. The solution was stirred for 0.5 h more at 20° C. and the solution was poured then to a mixture of ice and hydrochloric acid and extracted with ether. The ether extract was washed with water and extracted then with NaHCO3 -solution. The aqueous phase was acidified with hydrochloric acid and the semisolid product was separated and washed with water. Yield 7.3 g (55%).
Reference： [1]Current Patent Assignee: ORION OYJ - US4963590, 1990, A
  • 28
  • [ 86232-28-2 ]
  • [ 439291-60-8 ]
  • [ 1189527-93-2 ]
YieldReaction ConditionsOperation in experiment
In toluene for 5.5h; Molecular sieve; Reflux; 1 N-[1-(5-Chloro-2,3-dimethoxyphenyl)ethyl]-N-[5-fluoro-2-(methylthio)phenyl]amine (6); [Show Image] To a solution of the amine (10.0 g, 63.61 mmol) in toluene (140 mL) was added the aldehyde (17.86 g, 89.05 mmol) and 4 Å molecular sieves (32.0 g). After heating at reflux for 5.5 h using a Dean-Stark, the reaction mixture was cooled at -78 °C and MeLi (79.5 mL, 1.6 M solution in Et2O, 127.22 mmol) was added dropwise (30 min addition). The mixture was stirred at this temperature for 0.5 h, quenched with H2O (100 mL) and molecular sieves removed by filtration, washing with CH2Cl2 (2.0 L). Layers were separated and the aqueous layer was extracted with CH2Cl2 (2x75 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was flash chromatographed on silica gel (3% AcOEt/Hexanes) to give 19.43 g of the title product (Rf= 0.7 (10% AcOEt/Hexanes), pale yellow solid, 86% yield). 1H-NMR (CDCl3, 250 MHz, δ): 7.36 (dd, J = 8.2, 6.6 Hz, 1H, ArH); 6.84 (d, J = 2.5 Hz, 1H, ArH); 6.78 (d, J = 2.5 Hz, 1H, ArH); 6.28 (td, J = 8.5, 2.7 Hz, 1H, ArH); 6.08 (dd, J = 11.7, 2.7 Hz, 1H, ArH); 5.52 (d, J = 5.2 Hz, 1H, NH); 4.79 (q, J = 6.6 Hz, 1H, CH); 3.93 (s, 3H, OCH3); 3.86 (s, 3H, OCH3); 2.32 (s, 3H, SCH3); 1.53 (d, J = 6.6 Hz, 3H, CH3). MS-ES+ m/z: 356.2 (M+1).
Reference： [1]Current Patent Assignee: Corporacion Quimico Farmaceutica Esteve SA - EP2103596, 2009, A1 Location in patent: Page/Page column 38
  • 29
  • [ 86232-28-2 ]
  • [ 139192-88-4 ]
  • [ 1189527-90-9 ]
YieldReaction ConditionsOperation in experiment
In toluene for 6h; Molecular sieve; Reflux; 4 N-[5-Bromo-2-(methylthio)phenyl]-N-[1-(5-chloro-2,3-dimethoxyphenyl)ethyl]amine (22); [Show Image] To a solution of starting amine (0.213 g, 0.98 mmol) in toluene (5.0 mL) was added aldehyde (0.255 g, 1.27 mmol) and 4 Å molecular sieves (2.00 g). After heating at reflux for 6 h using a Dean-Stark, the reaction mixture was cooled at -78 °C and MeLi (1.2 mL, 1.6 M solution in Et2O, 1.92 mmol) added dropwise. The mixture was stirred at this temperature for 0.5 h, quenched with H2O (10 mL) and molecular sieves were removed by filtration. The mother liquors were extracted with AcOEt (3x10 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was flash chromatographed on silica gel (4% AcOEt/Hexanes) to give 0.330 g of the title product (Rf= 0.7 (10% AcOEt/Hexanes), pale yellow solid, 81% yield). 1P-NMR (CDCl3, 250 MHz, δ): 7.22 (d, J = 8.0 Hz, 1H, ArH); 6.84 (d, J = 2.2 Hz, 1H, ArH); 6.78 (d, J = 2.2 Hz, 1H, ArH); 6.72 (dd, J = 8.0, 2.0 Hz, 1H, ArH); 6.52 (d, J = 2.0 Hz, 1H, ArH); 5.35 (d, J = 6.5 Hz, 1H, NH); 4.82 (q, J = 6.5 Hz, 1H, CH); 3.95 (s, 3H, OCH3); 3.87 (s, 3H, OCH3); 2.34 (s, 3H, SCH3); 1.51 (d, J = 6.5 Hz, 3H, CH3).
Reference： [1]Current Patent Assignee: Corporacion Quimico Farmaceutica Esteve SA - EP2103596, 2009, A1 Location in patent: Page/Page column 49-50
  • 30
  • [ 1187659-03-5 ]
  • [ 86232-28-2 ]
  • [ 1189527-91-0 ]
YieldReaction ConditionsOperation in experiment
In toluene for 22h; Molecular sieve; Reflux; 2.2 The experimental procedure for Entry 2 is described below: [Show Image] To a solution of starting amine (1.602 g, 4.50 mmol) in toluene (60 mL) was added a solution of aldehyde (0.904 g, 4.50 mmol) in toluene (50 mL) and 4 Å molecular sieves (3.00 g). After heating at reflux for 6 h using a Dean-Stark, another portion of the aldehyde (0.093 g, 0.45 mmol) was added and the mixture stirred at the same temperature for another 16 h. Then, it was quickly concentrated, THF (110 mL) was added and the mixture was cooled at -78 °C. MeLi (8.4 mL, 1.6 M solution in Et2O, 13.50 mmol) was added dropwise (5 min addition) and the mixture stirred at this temperature for 2 h. The crude mixture was quenched with NH4Cl saturated aqueous solution (50 mL). Molecular sieves were filtered, mother liquors were extracted with AcOEt (4x100 mL) and the combined organic layers dried over anhydrous Na2SO4, filtered and concentrated. The crude was purified by medium flash chromatographed (Biotage system SP1, 15%→50% AcOEt/Hexanes) to give 0.863 g of the title product (Rf= 0.3 (2% MeOH/ CH2Cl2), white solid, 35% yield). 1H-NMR (CDCl3, 250 MHz, δ): 7.56 (s, 1H, ArH); 6.86 (d, J = 2.3 Hz, 1H, ArH); 6.76 (d, J = 2.3 Hz, 1H, ArH); 6.54 (d, J = 6.0 Hz, 1H, NH); 6.24 (dd, J = 8.9, 1.9 Hz, 1H, ArH); 5.97 (d, J = 1.9 Hz, 1H, ArH); 4.85 (q, J = 6.0 Hz, 1H, CH); 3.89 (s, 3H, OCH3); 3.85 (s, 3H, OCH3); 3.47 (m, 4H, CH2); 3.18 (m, 4H, CH2); 3.04 (s, 3H, SO2CH3); 1.54 (d, J = 6.0 Hz, 3H, CH3); 1.47 (s, 9H, Boc). MS-ES+ m/z: 554.8 (M+1).
Reference： [1]Current Patent Assignee: Corporacion Quimico Farmaceutica Esteve SA - EP2103596, 2009, A1 Location in patent: Page/Page column 43-44
  • 31
  • [ 86232-28-2 ]
  • [ 141-97-9 ]
  • [ 126-81-8 ]
  • [ 1372721-92-0 ]
YieldReaction ConditionsOperation in experiment
83% With ammonium acetate at 75℃; for 3h; Neat (no solvent);
Reference： [1]Location in patent: experimental part Siddaiah; Basha, G. Mahaboob; Rao, G. Padma; Prasad, U. Viplava; Rao, R. Suryachendra [Synthetic Communications, 2012, vol. 42, # 5, p. 627 - 634]
  • 32
  • [ 495-69-2 ]
  • [ 86232-28-2 ]
  • [ 1444008-97-2 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: Hippuric Acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 5-chloro-2,3-dimethoxybenzaldehyde In tetrahydrofuran at 75℃; for 0.266667h;
Reference： [1]Siddaiah; Basha, G. Mahaboob; Sudhakar; Srinuvasarao; Kumar, Y. Santosh [Synthetic Communications, 2013, vol. 43, # 16, p. 2191 - 2197]

Tags: 86232-28-2 synthesis path| 86232-28-2 SDS| 86232-28-2 COA| 86232-28-2 purity| 86232-28-2 application| 86232-28-2 NMR| 86232-28-2 COA| 86232-28-2 structure

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