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[ CAS No. 53242-88-9 ]

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Chemical Structure| 53242-88-9
Chemical Structure| 53242-88-9
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Product Details of [ 53242-88-9 ]

CAS No. :53242-88-9 MDL No. :MFCD02168779
Formula : C15H11ClN2O Boiling Point : 522.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :270.71 g/mol Pubchem ID :104452
Synonyms :

Safety of [ 53242-88-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53242-88-9 ]

  • Upstream synthesis route of [ 53242-88-9 ]
  • Downstream synthetic route of [ 53242-88-9 ]

[ 53242-88-9 ] Synthesis Path-Upstream   1~8

  • 1
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YieldReaction ConditionsOperation in experiment
90%
Stage #1: With hydrazine In ethanol at 85℃; for 15 h;
Stage #2: With acetone In ethanol at 2℃; for 2 h;
Intermediate 77 (Stage 2) <n="116"/>4-[4-chlorophenyl]methyl}-1(2H)-phthalazinone(3.pound.)-3-[(4-Chlorophenyl)methyhdene]-2-benzofuran-1 (3H)-one (as prepared, for example, in stage 1) (1 0 eq, corrected for loss on drying) is suspended in EtOH (3 7 vol) and heated to approximately 85 0C at slight reflux A solution of hydrazine hydrate (commercially available, for example, from Aldrich) (1 2 eq) in EtOH (O 63 vol) is added through a dropping funnel over 1 h At the end of the addition, EtOH (0 63 vol) is added through the dropping funnel into the reaction suspension in order to remove traces of hydrazine hydrate The reaction suspension is heated at approximately 85 0C at slight reflux for 14 h It is cooled to approximately 20 0C and a sample is taken to check the conversion (99percent conversion, HPLC) Acetone (0 35 vol) is added to the reaction mixture over 30 mm (exothermic reaction) The quenched suspension is stirred for at least 1 h and is then cooled to approximately 2 0C over 30 mm and stirred at approximately 2 0C for 1 h The product is isolated by filtration through a suction strainer and is washed with cold EtOH (approximately 0-5 0C, 3 x 1 9 vol) The pale brown solid is completely dried on the suction strainer in vacuo under nitrogen The title compound is obtained as a pale brown solid Yield (corrected for 1H NMR assay) 90-95percent1H MMR (400MHz, DMSO-Cf6), δ 4 30 (s, 2H), 7 35 (m, 4H), 7 88 (m, 3H), 8 26 (d, 1 H), 12 62 (s, 1 H)
Reference: [1] Patent: WO2007/122156, 2007, A1, . Location in patent: Page/Page column 114-115
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  • [ 105279-16-1 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 4075 - 4079
[2] Molecules, 2013, vol. 18, # 3, p. 3479 - 3501
[3] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 16, p. 2123 - 2126
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 10, p. 2786 - 2790
[5] Archiv der Pharmazie, 1988, vol. 321, # 4, p. 205 - 208
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  • [ 104-88-1 ]
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YieldReaction ConditionsOperation in experiment
24.8%
Stage #1: With sodium hydroxide In methanol; ethyl acetate at 80℃;
Stage #2: at 80℃;
Isobenzofuran-l(3H)-one (0.50 g, 1.0 eq.) was dissolved in methanol (2.0 mL) and ethyl acetate (10.0 mL) and then 4-chlorobenzaldehyde (0.52 g, 1.0 eq.) was added thereto. NaOH (0.60 g, 4.0 eq.) was dissolved in methanol (8.0 mL) and added to the reaction solution. The mixture was then stirred overnight at 80°C. After confirming the disappearance of the starting material by TLC, the reaction solution was concentrated under reduced pressure. Water and ethyl acetate were added to the obtained residue, and the extracted organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Hydrazine hydrate (20.0 mL) was added to the obtained residue, followed by stirring overnight at 80°C. The reaction solution was cooled at room temperature and concentrated under reduced pressure. Ethanol (10.0 mL) was added to the obtained residue and cooled to 0°C using ice. After confirming that a transparent red solid was crystallized, it was filtered to obtain the desired intermediate 4- (4-chlorobenzyl)phthalazin-l(2H)-one (0.25 g, yield 24.8percent).
Reference: [1] Patent: WO2018/80216, 2018, A1, . Location in patent: Page/Page column 56-57
  • 4
  • [ 2257-69-4 ]
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Reference: [1] Patent: US2011/124642, 2011, A1, . Location in patent: Page/Page column 41
  • 5
  • [ 20526-97-0 ]
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Reference: [1] Synthetic Communications, 2013, vol. 43, # 8, p. 1127 - 1137
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4052 - 4060
[3] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 16, p. 2769 - 2772
[4] Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1007 - 1012
[5] Patent: DE1046625, 1957, ,
  • 6
  • [ 1878-66-6 ]
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Reference: [1] Archiv der Pharmazie, 1988, vol. 321, # 4, p. 205 - 208
[2] Synthetic Communications, 2013, vol. 43, # 8, p. 1127 - 1137
[3] Molecules, 2013, vol. 18, # 3, p. 3479 - 3501
[4] Patent: WO2007/122156, 2007, A1,
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Reference: [1] Archiv der Pharmazie, 1988, vol. 321, # 4, p. 205 - 208
  • 8
  • [ 85-44-9 ]
  • [ 53242-88-9 ]
Reference: [1] Synthetic Communications, 2013, vol. 43, # 8, p. 1127 - 1137
[2] Molecules, 2013, vol. 18, # 3, p. 3479 - 3501
[3] Patent: WO2007/122156, 2007, A1,
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