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[ CAS No. 5367-32-8 ]

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Chemical Structure| 5367-32-8
Chemical Structure| 5367-32-8
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Product Details of [ 5367-32-8 ]

CAS No. :5367-32-8 MDL No. :MFCD00007167
Formula : C8H9NO3 Boiling Point : 280.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :167.16 g/mol Pubchem ID :79330
Synonyms :

Safety of [ 5367-32-8 ]

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

Application In Synthesis of [ 5367-32-8 ]

  • Upstream synthesis route of [ 5367-32-8 ]
  • Downstream synthetic route of [ 5367-32-8 ]

[ 5367-32-8 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 5367-32-8 ]
  • [ 10601-19-1 ]
Reference: [1] Journal of medicinal chemistry, 1995, vol. 38, # 13, p. 2331 - 2338
  • 2
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  • [ 102-50-1 ]
YieldReaction ConditionsOperation in experiment
80% at 80℃; for 8 h; General procedure: Nitro aromatic (1.0 mmol), B2(OH)4 (5.0 equiv, 5.0 mmol), and H2O (3.0 mL) were added in a10 mL tube. The reaction mixture was stirred at 80 °C for 8 h. When the reaction was completemonitored by TLC, the mixture was cooled to room temperature, extracted with ethyl acetate (3 ×20 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, andconcentrated under reduced pressure. The residue was purified by silica gel columnchromatography.
75% With tetrahydroxydiboron; 5%-palladium/activated carbon; water In acetonitrile at 50℃; for 24 h; General procedure: Nitrobenzene (0.6mmol), 5wtpercent Pd/C (0.5mmol percent, 0.003mmol), H2O (10 equiv, 6.0mmol), B2(OH)4 (3.3 equiv, 2.0mmol), and CH3CN (1.0mL) were added in a 10mL tube. The reaction mixture was stirred at 50°C for 24h. When the reaction was complete monitored by TLC, the mixture was cooled to room temperature. Water (5mL) was added, and extracted with EtOAc (3×5mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give aniline 2a (55mg, 99percent).
16.5 g With palladium on activated charcoal; hydrogen In methanol for 0.25 h; EXAMPLE 1396-((l-(2-(3-Fluoro-6-methoxy-8-methylquinolin-4-yl)ethyl)-2- oxabicyclo[2.2.2]octan-4-ylamino)methyl)-2H-pyrido[3,2-b][l,4]oxazin-3(4H)-oneStep 14-Methoxy-2-methylanilineA solution of 4-methoxy-2-methyl-l -nitrobenzene (20.0 g) in methanol (150 mL) was added Pd/C (1.0 g), then stirred under H2 for about 15 hours until the starting material disappeared on TLC. Filtered and the filtrate was concentrated under reduced pressure to give the title compound (16.5 g), which was used for the next step directly.
Reference: [1] Analytical Chemistry, 1992, vol. 64, # 8, p. 837 - 842
[2] ChemCatChem, 2017, vol. 9, # 16, p. 3236 - 3244
[3] Synlett, 2018, vol. 29, # 13, p. 1765 - 1768
[4] Tetrahedron, 2017, vol. 73, # 27-28, p. 3898 - 3904
[5] Helvetica Chimica Acta, 1924, vol. 7, p. 698
[6] Journal of the Chemical Society, 1923, vol. 123, p. 2989[7] Journal of the Chemical Society, 1924, vol. 125, p. 1305
[8] Journal of Organic Chemistry, 1951, vol. 16, p. 586,606
[9] Roczniki Chemii, vol. 6, p. 883[10] Chem. Zentralbl., 1927, vol. 98, # I, p. 3006
[11] Tetrahedron, 1978, vol. 34, p. 3611 - 3615
[12] Patent: WO2013/3383, 2013, A1, . Location in patent: Page/Page column 279
  • 3
  • [ 5367-32-8 ]
  • [ 6705-03-9 ]
Reference: [1] Synthetic Communications, 1994, vol. 24, # 4, p. 533 - 548
  • 4
  • [ 5367-32-8 ]
  • [ 1882-69-5 ]
Reference: [1] Synthetic Communications, 1994, vol. 24, # 4, p. 533 - 548
[2] Journal of the Chemical Society, 1923, vol. 123, p. 1272
  • 5
  • [ 5367-32-8 ]
  • [ 95-92-1 ]
  • [ 20876-29-3 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 25, p. 8447 - 8453
[2] Journal of Natural Products, 2015, vol. 78, # 7, p. 1536 - 1542
[3] Tetrahedron, 1968, vol. 24, p. 6093 - 6109
[4] Tetrahedron, 1990, vol. 46, # 16, p. 5555 - 5562
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