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[ CAS No. 57319-65-0 ]

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2D
Chemical Structure| 57319-65-0
Chemical Structure| 57319-65-0
Structure of 57319-65-0 *Storage: {[proInfo.prStorage]}

Quality Control of [ 57319-65-0 ]

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Product Details of [ 57319-65-0 ]

CAS No. :57319-65-0MDL No. :MFCD00033530
Formula :C8H7NO2Boiling Point :420.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :149.15Pubchem ID :93631
Synonyms :

Computed Properties of [ 57319-65-0 ]

TPSA : 52.3 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.13 Rotatable Bond Count : 0

Safety of [ 57319-65-0 ]

Signal Word:WarningClass
Precautionary Statements:P261-P280-P305 P351 P338-P304 P340-P405-P501UN#:
Hazard Statements:H315-H319-H335Packing Group:
GHS Pictogram:

Application In Synthesis of [ 57319-65-0 ]

  • Upstream synthesis route of [ 57319-65-0 ]
  • Downstream synthetic route of [ 57319-65-0 ]

[ 57319-65-0 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
87% With hydrogen In tetrahydrofuran; methanol at 20℃; for 20.00 h; Commercially available 6-nitro-1(3H)-isobenzofuranone (9.9 g, 55 mmol) was dissolved in a mixed solvent of tetrahydrofuran (20 ml)-methanol (60 ml), then 5percent palladium-charcoal catalyst (1.5 g) was added thereto, and the mixture was stirred at room temperature for 20 hours under an atmosphere of hydrogen gas. The reaction mixture was filtered, and the solid was washed successively with ethyl acetate and methanol. The filtrate and washings were combined, and the resulting solution was concentrated under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (6.21 g) as a crystalline solid. The washings were concentrated, and the residue was crystallized from a mixed solvent of ethyl acetate-hexane to give an additional amount of the title compound (0.95 g, total yield 87percent). NMR spectrum (400 MHz, CD3OD) δ ppm: 5.225 (2H, s), 7.060 (1H, d-like, J=2 Hz), 7.071 (1H, dd-like, J=9, 2 Hz), 7.288 (1H, d, J=9 Hz) IR spectrum ν max KBr cm-1: 3473, 3372, 3278, 1735, 1631, 1504, 1330, 1059, 992.
86% With palladium on carbon; hydrogen In methanol at 20℃; for 12.00 h; 6-Nitro-3H-isobenzofuran-1-one 1)> (2.00 g, 11.1 mmol) was dissolved in methanol (25 ml), and 20percent palladium/ carbon (200 mg) was added thereto, followed by stirring at room temperature for 12 hours in the presence of hydrogen gas (50 psi). The reaction solution was filtered and concentrated under reduced pressure to obtain the title compound (1.43 g, 86percent). [1326] 1H NMR (400 MHz, DMSO-d6): δ 7.30 (d, J=8.0 Hz, 1H), 6.96 (dd, J=8.0, 2.0 Hz, 1H), 6.91 (d, J=4.0 Hz, 1H), 5.56 (s, 2H), 5.21 (s, 2H)
78% With hydrogenchloride; tin(ll) chloride In water for 4.00 h; Heating / reflux Step b:
6-Aminoisobenzofuran-1(3H)-one
To a solution of 6-nitroisobenzofuran-1(3H)-one (15 g, 0.080 mol) in HCl/H2O (375 mL/125 mL) was added SnCl2.2H2O (75 g, 0.33 mol).
The reaction mixture was heated at reflux for 4 h before it was quenched with water and extracted with EtOAc (300 mL*3).
The organics were dried over Na2SO4 and evaporated in vacuo to give 6-aminoisobenzofuran-1(3H)-one (10 g, 78percent).
1H NMR (300 MHz, CDCl3) δ 7.23 (d, J=8.1, 1H), 7.13 (d, J=2.1, 1H), 6.98 (dd, J=8.1, 2.1, 1H), 5.21 (s, 2H), 3.99 (br s, 2H).
78% With hydrogenchloride; tin(II) chloride dihdyrate In water for 4.00 h; Reflux To a solution of 6-nitroisobenzofuran-1(3H)-one (15 g, 0.080 mol) in HCl/H2O (375 mL/125 mL) was added SnCl2.2H2O (75 g, 0.33 mol).
The reaction mixture was heated at reflux for 4 h before it was quenched with water and extracted with EtOAc (300 mL*3).
The organics were dried over Na2SO4 and evaporated in vacuo to give 6-aminoisobenzofuran-1(3H)-one (10 g, 78percent).
1H NMR (300 MHz, CDCl3) δ 7.23 (d, J=8.1, 1H), 7.13 (d, J=2.1, 1H), 6.98 (dd, J=8.1, 2.1, 1H), 5.21 (s, 2H), 3.99 (br s, 2H).
75% With indium (III) iodide; 1,1,3,3-Tetramethyldisiloxane In toluene at 60℃; for 4.00 h; Inert atmosphere; Sealed tube General procedure: To a screw top vial (5 mL) under N2 containing freshly distilled toluene (0.6 mL) were successively added an aromatic nitro compound (0.60 mmol), InI3 (14.9 mg, 0.030 mmol), and TMDS (318 μL, 1.80 mmol). After the vial was sealed with a cap that contained a PTFE septum, the mixture was stirred at 60 °C (bath temperature), and monitored via TLC analysis. Sat. aq NaHCO3 solution (5 mL) was added to the resultant mixture, which was then extracted with EtOAc (3 × 6 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (n-hexane–EtOAc, 9:1 to 4:1) to afford the corresponding aniline derivative.

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  • [ 610-93-5 ]
  • [ 10025-69-1 ]
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Reference: [1] Patent: US2011/98311, 2011, A1
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  • [ 87-41-2 ]
  • [ 57319-65-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1195 - 1204
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3417 - 3423
[3] Chemische Berichte, 1934, vol. 67, p. 675,681
[4] Chemical Biology and Drug Design, 2010, vol. 76, # 1, p. 25 - 33
[5] Patent: US2011/98311, 2011, A1
[6] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 4, p. 1063 - 1069
[7] Patent: US2015/51395, 2015, A1
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3997 - 4015
[9] Patent: US2015/231142, 2015, A1
  • 4
  • [ 5466-84-2 ]
  • [ 57319-65-0 ]
Reference: [1] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 229 - 238
  • 5
  • [ 85-44-9 ]
  • [ 57319-65-0 ]
Reference: [1] Chemical Biology and Drug Design, 2010, vol. 76, # 1, p. 25 - 33
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