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[ CAS No. 610-93-5 ]

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Chemical Structure| 610-93-5
Chemical Structure| 610-93-5
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CAS No. :610-93-5 MDL No. :MFCD00033529
Formula : C8H5NO4 Boiling Point : 413.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :179.13 g/mol Pubchem ID :223584
Synonyms :

Safety of [ 610-93-5 ]

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

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[ 610-93-5 ] Synthesis Path-Upstream   1~19

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Reference: [1] Chemische Berichte, 1934, vol. 67, p. 675,681
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3997 - 4015
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YieldReaction ConditionsOperation in experiment
87% With hydrogen In tetrahydrofuran; methanol at 20℃; for 20 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 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 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 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 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.

Reference: [1] Physical Chemistry Chemical Physics, 2005, vol. 7, # 24, p. 4070 - 4081
[2] Chemistry - A European Journal, 2016, vol. 22, # 13, p. 4600 - 4607
[3] ACS Catalysis, 2014, vol. 4, # 10, p. 3504 - 3511
[4] Patent: EP1362856, 2003, A1, . Location in patent: Page/Page column 159
[5] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1195 - 1204
[6] Catalysis Letters, 2014, vol. 144, # 7, p. 1258 - 1267
[7] Patent: US2015/51395, 2015, A1, . Location in patent: Paragraph 1325-1326
[8] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 6, p. 1519 - 1523
[9] Patent: US2008/9524, 2008, A1, . Location in patent: Page/Page column 409; 409-410
[10] Journal of Organic Chemistry, 2009, vol. 74, # 18, p. 6960 - 6964
[11] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 1264
[12] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 229 - 238
[13] Chemistry of Heterocyclic Compounds, 2010, vol. 46, # 2, p. 140 - 145
[14] Synthesis (Germany), 2015, vol. 47, # 20, p. 3179 - 3185
[15] Journal of the American Chemical Society, 1937, vol. 59, p. 864
[16] Patent: US2130480, 1935, ,
[17] Chemische Berichte, 1934, vol. 67, p. 675,681
[18] Tetrahedron, 1988, vol. 44, # 14, p. 4591 - 4604
[19] Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3417 - 3423
[20] Patent: US4409017, 1983, A,
[21] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 8, p. 3177 - 3188
[22] Chemical Biology and Drug Design, 2010, vol. 76, # 1, p. 25 - 33
[23] Organic Letters, 2012, vol. 14, # 14, p. 3748 - 3751
[24] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 4, p. 1063 - 1069
[25] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1269 - 1273
[26] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3997 - 4015
[27] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 22, p. 5929 - 5940
[28] European Journal of Organic Chemistry, 2018, vol. 2018, # 2, p. 209 - 214
[29] Applied Catalysis A: General, 2018, vol. 559, p. 127 - 137
[30] Research on Chemical Intermediates, 2018, vol. 44, # 9, p. 5107 - 5122
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  • [ 10025-69-1 ]
  • [ 57319-65-0 ]
Reference: [1] Patent: US2011/98311, 2011, A1,
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  • [ 610-93-5 ]
  • [ 19477-73-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1195 - 1204
[2] Chemistry of Heterocyclic Compounds, 2010, vol. 46, # 2, p. 140 - 145
[3] Patent: US2011/98311, 2011, A1,
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3997 - 4015
[5] Patent: US2015/231142, 2015, A1,
  • 5
  • [ 610-93-5 ]
  • [ 53910-10-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1195 - 1204
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 4, p. 1063 - 1069
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3997 - 4015
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  • [ 87-41-2 ]
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YieldReaction ConditionsOperation in experiment
94% at 20℃; Cooling with ice Step A: Synthesis of 6-nitrobenzofuran-l(3H)-one[0086] To an ice-cold stirred solution of phthalide (40.0 g, 298 mmol) in sulfuric acid (50.0 mL) was added potassium nitrate (30.4 g, 300 mmol) dissolved in sulfuric acid (80 mL) via dropwise addition. The reaction was stirred and allowed to warm to room temperature over 5 h. The resulting mixture was poured into ice-water, and the precipitate collected was recrystallized from ethanol (3 L) to afford 6-nirobenzofuran-l(3H)-one (50.4 g, 94percent) as an off-white solid (98percent of the desired regioisomer by NMR): 1H NMR (500 MHz, CDC13) δ 8.77 (d, J= 1.5 Hz, 1H), 8.58 (dd, J= 8.5, 2.0 Hz, 1H), 7.72 (d, J- 8.5 Hz, 1H), 5.45 (s, 2H).
80% With sulfuric acid; potassium nitrate In water at 0 - 20℃; for 1 h; Step a:
6-Nitroisobenzofuran-1(3H)-one
To a stirred solution of 3H-isobenzofuran-1-one (30.0 g, 0.220 mol) in H2SO4 (38 mL) was added KNO3 (28.0 g, 0.290 mol) in H2SO4 (60 mL) at 0° C.
The mixture was stirred at 20° C. for 1 h.
The reaction mixture was poured into ice and the resulting precipitate was filtered off.
The solid was recrystallized from ethanol to give 6-nitroisobenzofuran-1(3H)-one (32.0 g, 80percent).
1H NMR (300 MHz, CDCl3) δ 8.76 (d, J=2.1, 1H), 8.57 (dd, J=8.4, 2.1, 1H), 7.72 (d, J=8.4, 1H), 5.45 (s, 2H).
80% at 0 - 20℃; for 1 h; 6-Nitroisobenzofuran-1(3H)-one
To a stirred solution of 3H-isobenzofuran-1-one (30.0 g, 0.220 mol) in H2SO4 (38 mL) was added KNO3 (28.0 g, 0.290 mol) in H2SO4 (60 mL) at 0° C.
The mixture was stirred at 20° C. for 1 h.
The reaction mixture was poured into ice and the resulting precipitate was filtered off.
The solid was recrystallized from ethanol to give 6-nitroisobenzofuran-1(3H)-one (32.0 g, 80percent).
1H NMR (300 MHz, CDCl3) δ 8.76 (d, J=2.1, 1H), 8.57 (dd, J=8.4, 2.1, 1H), 7.72 (d, J=8.4, 1H), 5.45 (s, 2H).
37% at 0 - 20℃; for 5 h; 3H-Isobenzofuran-1-one (4.00 g, 29.8 mmol) was dissolved in concentrated sulfuric acid (5.0 ml) at 0° C., and a solution of potassium nitrate (3.0 g, 30 mmol) in concentrated sulfuric acid (8.0 ml) was added dropwise thereto. After stirring at room temperature for 5 hours, the reaction solution was diluted with water. The precipitated solid was filtered and recrystallized from ethanol (20 ml) to obtain the title compound (2.0 g, 37percent). [1323] 1H NMR (400 MHz, DMSO-d6): δ 8.62-8.59 (m, 1H), 8.53 (d, J=2.8 Hz, 1H), 7.72 (d, J=8.0 Hz, 1H), 5.57 (s, 2H)
1 g at 0℃; for 0.5 h; To a solution of phthalide (2.5 g, 18.65 mmol) in conc.H2S04 was added a solution of potassium nitrate (2.22 g, 18.65 mmol) in cone. H2S04. The reaction mixture was stirred at 0°C for 30 minutes and quenched with water and filtered. The filtrate was concentrated and purified by column chromatography to afford 1.00 g of the title product. 1H NMR (300 MHz, DMSO-Je): δ 5.45 (s, 2H), 7.72 (d, / = 8.4 Hz, 1H), 8.58 (d, / = 8.1 Hz, 1H), 8.78 (s, 1H).

Reference: [1] Journal fuer Praktische Chemie/Chemiker-Zeitung, 1993, vol. 335, # 1, p. 17 - 22
[2] Patent: WO2012/142459, 2012, A1, . Location in patent: Page/Page column 37
[3] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 6, p. 1519 - 1523
[4] Patent: US2008/9524, 2008, A1, . Location in patent: Page/Page column 409
[5] Patent: US2011/98311, 2011, A1,
[6] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 1263
[7] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 7, p. 2809 - 2820
[8] Patent: US2015/51395, 2015, A1, . Location in patent: Paragraph 1322-1323
[9] Recueil des Travaux Chimiques des Pays-Bas, 1923, vol. 42, p. 37
[10] Chemische Berichte, 1885, vol. 18, p. 3452
[11] Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3417 - 3423
[12] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1195 - 1204
[13] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 8, p. 3177 - 3188
[14] Chemical Biology and Drug Design, 2010, vol. 76, # 1, p. 25 - 33
[15] Chemistry of Heterocyclic Compounds, 2010, vol. 46, # 2, p. 140 - 145
[16] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 4, p. 1063 - 1069
[17] Patent: WO2013/72825, 2013, A1, . Location in patent: Page/Page column 33; 34
[18] Journal of Medicinal Chemistry, 2014, vol. 57, # 4, p. 1495 - 1512
[19] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3997 - 4015
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Reference: [1] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 229 - 238
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  • [ 1445-69-8 ]
  • [ 610-93-5 ]
Reference: [1] Heterocycles, 1982, vol. 18, p. 327 - 341
[2] Heterocycles, 1982, vol. 18, p. 327 - 341
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 7, p. 2809 - 2820
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Reference: [1] Chemische Berichte, 1898, vol. 31, p. 2734
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  • [ 67081-02-1 ]
Reference: [1] ChemCatChem, 2014, vol. 6, # 1, p. 109 - 112
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  • [ 60-34-4 ]
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Reference: [1] Heterocycles, 1982, vol. 18, p. 327 - 341
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  • [ 610-93-5 ]
  • [ 65399-18-0 ]
Reference: [1] Chemische Berichte, 1934, vol. 67, p. 675,681
[2] Bulletin de la Societe Scientifique de Bretagne, 1951, vol. 26, p. Sonderheft 5, S. 7, 96[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1952, vol. 235, p. 962
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  • [ 67081-02-1 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 7, p. 2809 - 2820
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Reference: [1] Chemische Berichte, 1934, vol. 67, p. 675,681
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  • [ 87-41-2 ]
  • [ 7664-93-9 ]
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1923, vol. 42, p. 37
[2] Chemische Berichte, 1885, vol. 18, p. 3452
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  • [ 7647-01-0 ]
  • [ 121996-04-1 ]
  • [ 64-19-7 ]
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Reference: [1] Helvetica Chimica Acta, 1931, vol. 14, p. 541,545
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  • [ 7697-37-2 ]
  • [ 610-27-5 ]
Reference: [1] Chemische Berichte, 1885, vol. 18, p. 3452
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  • [ 4506-45-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1195 - 1204
[2] Chemistry of Heterocyclic Compounds, 2010, vol. 46, # 2, p. 140 - 145
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