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[ CAS No. 101084-96-2 ]

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Chemical Structure| 101084-96-2
Chemical Structure| 101084-96-2
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Product Details of [ 101084-96-2 ]

CAS No. :101084-96-2 MDL No. :MFCD02093781
Formula : C8H6N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :178.14 g/mol Pubchem ID :-
Synonyms :

Safety of [ 101084-96-2 ]

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

Application In Synthesis of [ 101084-96-2 ]

  • Upstream synthesis route of [ 101084-96-2 ]
  • Downstream synthetic route of [ 101084-96-2 ]

[ 101084-96-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 4110-33-2 ]
  • [ 124-41-4 ]
  • [ 38469-83-9 ]
  • [ 101084-96-2 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1992, # 6, p. 1371 - 1382
[2] Patent: US2015/329556, 2015, A1, . Location in patent: Paragraph 1554
  • 2
  • [ 101084-96-2 ]
  • [ 67608-58-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 3, p. 668 - 671
  • 3
  • [ 101084-96-2 ]
  • [ 7251-09-4 ]
YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen In methanol at 0.1 - 35℃; for 48 h; (Step 1)
A solution of 2-methoxy-4-nitrobenzonitrile (750 mg, 4.21 mmol) and palladium on carbon (50 mg, 0.47 mmol) in methanol (15 mL) was stirred at room temperature for 48 hr under hydrogen atmosphere (1 atm).
The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to give 4-amino-2-methoxybenzonitrile (679 mg, 4.58 mmol, quantitative) as a brownish-red powder.
1H-NMR(300MHz,DMSO-d6): δ3.32(3H,s), 6.05-6.29(4H,m), 7.23(1H,d,J=8.3Hz).
96% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 5.5 h; General procedure: Compound 13a (221 mg, 1.05 mmol) was dissolved in MeOH (8.0 mL) and hydrogenated (1 bar H2) over 10percent palladium on charcoal for 5.5 h at r.t. The mixture was filtered through a pad of Celite and the filtrate was concentrated. The residue was recrystallized from DCM and n-hexane to afford the title compound (193 mg, 1.05 mmol, quant.) as a white solid.
73% With hydrogenchloride; iron In ethanol; water at 20℃; for 3 h; Reference Example 7
4-amino-2-methoxybenzonitrile
2-Methoxy-4-nitrobenzonitrile (5.0 g) and iron powder (7.84 g) were suspended in ethanol (150 mL), and concentrated hydrochloric acid (35 mL) was added dropwise at room temperature.
The reaction mixture was stirred at room temperature for 3 hr, neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate.
The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
The residue was purified by silica gel column chromatography, and the obtained solid was washed with hexane to give the title compound as a red-brown solid (yield: 3.05 g, 73percent).
1H-NMR(CDCl3)δ:3.86(3H,s), 4.15(2H,brs), 6.16(1H,d,J=2.1 Hz), 6.22(1H,dd,J=8.3,2.1 Hz), 7.30(1H,d,J=8.3 Hz).
Reference: [1] Patent: EP2759533, 2014, A1, . Location in patent: Paragraph 0484; 0485
[2] Synthesis, 2006, # 19, p. 3316 - 3340
[3] Chemistry - A European Journal, 2014, vol. 20, # 31, p. 9504 - 9509
[4] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 10, p. 979 - 988
[5] Patent: US2009/42967, 2009, A1, . Location in patent: Page/Page column 22
[6] Journal of the American Chemical Society, 1952, vol. 74, p. 2226,2235
[7] Journal of the Chemical Society, 1945, p. 861,864
[8] Journal of Medicinal Chemistry, 2001, vol. 44, # 23, p. 3856 - 3871
[9] Patent: US2004/77605, 2004, A1,
[10] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 1926 - 1930
[11] Patent: WO2011/72488, 2011, A1, . Location in patent: Page/Page column 17; 36-37
[12] Patent: US2012/283297, 2012, A1, . Location in patent: Page/Page column 22
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