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[ CAS No. 58142-97-5 ]

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2D
Chemical Structure| 58142-97-5
Chemical Structure| 58142-97-5
Structure of 58142-97-5 *Storage: {[proInfo.prStorage]}

Quality Control of [ 58142-97-5 ]

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Related Doc. of [ 58142-97-5 ]

SDS

Product Details of [ 58142-97-5 ]

CAS No. :58142-97-5MDL No. :MFCD11052590
Formula :C9H5ClN2O2Boiling Point :-
Linear Structure Formula :-InChI Key :N/A
M.W :208.60Pubchem ID :459774
Synonyms :

Computed Properties of [ 58142-97-5 ]

TPSA : 58.7 H-Bond Acceptor Count : 3
XLogP3 : 2.9 H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 58142-97-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 58142-97-5 ]

  • Upstream synthesis route of [ 58142-97-5 ]
  • Downstream synthetic route of [ 58142-97-5 ]

[ 58142-97-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 57554-78-6 ]
  • [ 58142-97-5 ]
YieldReaction ConditionsOperation in experiment
89% With trichlorophosphate In dichloromethane; N,N-dimethyl-formamide at 0 - 25℃; Inert atmosphere General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1M) at 0 °C is added POCl3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7~8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (80:1) as eluent.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 51, p. 7130 - 7132
  • 2
  • [ 19493-44-8 ]
  • [ 58142-97-5 ]
YieldReaction ConditionsOperation in experiment
4 g at 0 - 26℃; for 2.00 h; To a solution of 1-chloroisoquinoline (3.6 g, 22.09 mmol) in conc. H2SO4 (24 mL) was added conc. HNO3 (8 mL) drop wise at 0-5° C. Then KNO3 (2.90 g, 28.71 mmol) was added to the reaction mixture portion wise at 0-5° C.
The reaction mass was stirred at rt for 2 h and diluted with water then the reaction mixture was filtered.
The filter cake was dissolved in 5percent methanol in chloroform and was dried over Na2SO4.
The organic layer was filtered and concentrated to afford 4.0 g of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.74 (t, J=6.9 Hz, 2H), 8.55 (d, J=6.3 Hz, 1H), 8.32 (d, J=6.0 Hz, 1H), 8.02 (t, J=8.1 Hz, 1H).
Reference: [1] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 11, p. 3635 - 3639
[2] Chemical and Pharmaceutical Bulletin, 2013, vol. 61, # 7, p. 747 - 756
[3] Journal of Medicinal Chemistry, 2002, vol. 45, # 3, p. 740 - 743
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2049 - 2059
[5] Journal of the American Chemical Society, 1946, vol. 68, p. 1436
[6] Journal of the American Pharmaceutical Association (1912-1977), 1952, vol. 41, p. 643,648
[7] Journal of the American Chemical Society, 1947, vol. 69, p. 1939,1941
[8] Patent: US2006/194801, 2006, A1. Location in patent: Page/Page column 53
[9] Patent: US2006/205773, 2006, A1. Location in patent: Page/Page column 30
[10] Patent: WO2007/5668, 2007, A2. Location in patent: Page/Page column 33; 46
[11] Patent: US2013/210844, 2013, A1. Location in patent: Paragraph 0264-0266
  • 3
  • [ 20141-83-7 ]
  • [ 82827-08-5 ]
  • [ 244219-94-1 ]
  • [ 58142-97-5 ]
Reference: [1] Patent: EP1228043, 2005, B1. Location in patent: Page/Page column 7
  • 4
  • [ 491-30-5 ]
  • [ 58142-97-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 3, p. 740 - 743
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