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[ CAS No. 641-70-3 ]

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Chemical Structure| 641-70-3
Chemical Structure| 641-70-3
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CAS No. :641-70-3 MDL No. :MFCD00005921
Formula : C8H3NO5 Boiling Point : 411.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :193.11 g/mol Pubchem ID :21631
Synonyms :

Safety of [ 641-70-3 ]

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:

Application In Synthesis of [ 641-70-3 ]

  • Upstream synthesis route of [ 641-70-3 ]
  • Downstream synthetic route of [ 641-70-3 ]

[ 641-70-3 ] Synthesis Path-Upstream   1~26

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Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937
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  • [ 6296-53-3 ]
Reference: [1] Annales Pharmaceutiques Francaises, 1958, vol. 16, p. 421,425
  • 3
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  • [ 59434-19-4 ]
Reference: [1] Patent: WO2011/130661, 2011, A1,
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  • [ 2518-24-3 ]
Reference: [1] Chemische Berichte, 1903, vol. 36, p. 2496
[2] Journal of the Chemical Society, 1937, p. 26,31
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YieldReaction ConditionsOperation in experiment
88.8% for 1 h; Heating / reflux A solution of 474.8 g (2.25 mol) of 3-nitrophthalic acid in 450 ml of acetic anhy- dride was stirred under reflux for 1 h. The solution was slowly cooled to 800C. Then 1000 ml of methyl-tert-butyl ether (MTBE) were added expeditiously and the solution EPO <DP n="34"/>was cooled to 15°C. The resulting solid was isolated, washed with MTBE and dried in a vacuum oven at 400C. Yield: 88.8percent
88% With oxalyl dichloride; N,N-dimethyl-formamide In toluene for 3 h; Inert atmosphere; Reflux General procedure: Dicarboxylic acid 2 (1 mmol) and oxalyl chloride (1.2 mmol) were combined in dry toluene (5 mL) and a drop of freshly distilled DMF was added. The reaction vessel was purged with argon and the reaction was heated under stirring for 3 h. The stirring was stopped and the toluene solution was decanted off the oily residue and filtered. Evaporation of the volatiles provided the analytically pure target product which, if necessary, was transformed intro crystalline form by trituration with diethyl ether. In some cases (see ESI) additional crystallization or trituration with 1:2 v/v hexane-toluene mixture was used. .
82% With acetic anhydride In tert-butyl methyl ether for 1 h; Reflux (1)
Synthesis of 3-nitrophthalic anhydride (compound 2)
3-nitrophthalic acid (48.5 g, 0.23 mol) was mixed with acetic anhydride (45 mL), and the resulting mixture was stirred at reflux for 1 hour.
After completion of the reaction, the mixture was cooled to 80° C., 100 mL of methyl tert-butyl ether was added to the mixture, and the mixture was continued to stir until cooled to 15° C.
The mixture was filtered, and the resulted solid was washed with methyl tert-butyl ether and dried at 40° C. to give compound 2 as a white product (36.7 g, 82percent).
74.0 g With acetic anhydride In toluene at 25℃; Reflux In to a well cleaned and 1.0L 4neck RB flask, 100.0g of 3-nitrophthalic acid and 60.36g of acetic anhydride, 500.0m1 of toluene were charged. Reaction mass was stirred for 5-10mm at 25-35°C.Reaction mass temperature was raised to reflux and maintained for 20-30min.after completion of reaction, reaction mass was cooled to 25-35°C, Reaction mass was stirred for 60-90 mm at 25-35°C. Solid reaction mass was filtered under vacuum, washing was given with40.0m1 of toluene, suck dried for 10-15mm. Wet compound was unloaded. Wet compound is dried in a vacuum oven, at 60-65°C, for 3.0-4.0 hours, under vacuum (600-65OmmJHg). Dried sample is transferred into a clean and dry polythene bag under nitrogen.Yield: 74.0g.

Reference: [1] Organic Letters, 2010, vol. 12, # 21, p. 4796 - 4799
[2] Bioorganic Chemistry, 2018, vol. 81, p. 373 - 381
[3] Synthetic Communications, 2016, vol. 46, # 16, p. 1343 - 1348
[4] Patent: WO2007/6566, 2007, A1, . Location in patent: Page/Page column 28; 32-33
[5] Tetrahedron Letters, 2017, vol. 58, # 32, p. 3160 - 3163
[6] Organic Process Research and Development, 2007, vol. 11, # 4, p. 693 - 698
[7] Patent: US2018/134722, 2018, A1, . Location in patent: Paragraph 0019
[8] Journal of the American Chemical Society, 1901, vol. 23, p. 751
[9] Chemische Berichte, 1902, vol. 35, p. 472,3859
[10] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1878, vol. 10, p. 192[11] Justus Liebigs Annalen der Chemie, 1881, vol. 208, p. 225
[12] Justus Liebigs Annalen der Chemie, 1842, vol. 41, p. 107,110
[13] Journal of the Chemical Society, 1901, vol. 79, p. 1137
[14] Monatshefte fuer Chemie, 1900, vol. 21, p. 794
[15] Journal of the Chemical Society, 1925, vol. 127, p. 1794
[16] Helvetica Chimica Acta, 1922, vol. 5, p. 10[17] Helvetica Chimica Acta, 1923, vol. 6, p. 419 Anm. 2
[18] Journal of the American Chemical Society, 1920, vol. 42, p. 1876
[19] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1834 - 1840
[20] Synthetic Communications, 1985, vol. 15, # 6, p. 485 - 490
[21] Bulletin des Societes Chimiques Belges, 1996, vol. 105, # 1, p. 55 - 56
[22] Pest Management Science, 2001, vol. 57, # 3, p. 205 - 224
[23] Patent: US3979416, 1976, A,
[24] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 1, p. 285 - 288
[25] Journal of Organic Chemistry, 2010, vol. 75, # 2, p. 368 - 374
[26] Patent: WO2007/100295, 2007, A1, . Location in patent: Page/Page column 252
[27] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 8, p. 2641 - 2649
[28] Patent: WO2011/141909, 2011, A2, . Location in patent: Page/Page column 32-34
[29] Letters in Organic Chemistry, 2013, vol. 10, # 7, p. 496 - 501
[30] Coll. Vol. 1 &lt;New York 1932&gt;, S. 402,
[31] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 5, p. 1337 - 1342
[32] European Journal of Medicinal Chemistry, 2015, vol. 106, p. 106 - 119
[33] Patent: CN104402863, 2016, B, . Location in patent: Paragraph 0035
[34] Patent: WO2017/221261, 2017, A1, . Location in patent: Page/Page column 5
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  • [ 88-99-3 ]
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Reference: [1] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 229 - 238
[2] Journal of the American Chemical Society, 1920, vol. 42, p. 1876
[3] Journal of the American Chemical Society, 1901, vol. 23, p. 751
[4] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1878, vol. 10, p. 192[5] Justus Liebigs Annalen der Chemie, 1881, vol. 208, p. 225
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Reference: [1] Journal of the American Chemical Society, 1901, vol. 23, p. 751
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Reference: [1] Journal of the American Chemical Society, 1920, vol. 42, p. 1876
[2] Letters in Organic Chemistry, 2013, vol. 10, # 7, p. 496 - 501
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Reference: [1] Justus Liebigs Annalen der Chemie, 1842, vol. 41, p. 107,110
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  • [ 24666-56-6 ]
  • [ 19171-18-7 ]
YieldReaction ConditionsOperation in experiment
89.7% at 25 - 118℃; for 18 h; A round bottom flask was charged with a solution of glacial acetic acid (75 ml) and α-amino glutarimide hydrochloride (8.5 g).
Sodium acetate anhydrous (4.5 g) was added lot-wise to the solution at 25° C. to 30° C. followed by addition of 3-nitro phthalic anhydride (log) at the same temperature.
The reaction mixture was stirred at 118° C. for 18 hr.
After the completion of reaction, the reaction mass was cooled to 60° C. and the solvent was distilled off under vacuum to get the residue.
To the residue obtained, water (100 ml) was added; the mixture was stirred for 1 hr at 25° C. to 30° C. and the mass filtered.
The wet cake obtained was slurried with water (100 ml*2), filtered and dried in an air tray dryer until the water content was less than 0.5percent to afford 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione (14 g). Yield: 89.7percent, Purity: 98percent.
88.3% With sodium acetate; acetic acid In water at 116 - 118℃; for 17 h; In the 2L reaction bottle into the water 60ml, 3-nitrophthalic anhydride 65 g (336.6 mmol), 3-aminopiperidine-2,6-dione hydrochloride 53.5 g (325.0 mmol) Sodium acetate 27 g (329.3 mmol) and acetic acid (1200 ml) The reaction was stirred at 116-118 ° C for 17 h, Cooled to room temperature, filtered, Filter cake water washing, Solid at 50-60 decompression (vacuum ≥ 0.08MPa) dry 5h, That is the target product 87g, silver-gray solid, The yield was 88.3percent and the purity was 99.88percent.
Reference: [1] Patent: US2017/260157, 2017, A1, . Location in patent: Page/Page column 5
[2] Patent: CN104926786, 2017, B, . Location in patent: Paragraph 0044; 0045
[3] Synthetic Communications, 2016, vol. 46, # 16, p. 1343 - 1348
[4] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 11, p. 1625 - 1630
[5] Patent: CN104402863, 2016, B, . Location in patent: Paragraph 0035
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YieldReaction ConditionsOperation in experiment
84.2%
Stage #1: With triethylamine In toluene for 8 h; Reflux
Stage #2: With 1,1'-carbonyldiimidazole In toluene at 20 - 25℃; for 2 h;
In a mixer equipped with a mechanical stirrer, (0.124 mol, 1.069) of 3-nitrophthalic anhydride, 21.5 g (0.130 mol, 1.05 eq) of 3-aminopiperidine-2,6-diamine were added to a 500 mL four-necked flask equipped with a thermometer and a water separator. (0.148 mol, 1.2 eq) of triethylamine was added and the mixture was gradually warmed up to reflux to separate water. The reaction solution was changed to a purple suspension, and the mixture was refluxed for a further period of time Water for 8 hours, HPLC control: to be 3-nitrophthalic anhydride content of raw materials <0.5percent, the reaction temperature dropped to 20 ~ 25 ° C, the reactor by adding 6.0g N, N'-carbonyl (0.037mol, 0.3eq), slowly heated to reflux stirring 2 hours, HPLC control: to be intermediate content <0.5percent, the reaction solution to 20 ~ 25 ° C when the filter, the mother liquor retained to apply, filter cake Into another 250mL reaction bottle, add 60mL of methanol and 60mL of water mixture beating for 2 hours, filtration, the light purple solid wet weight 48.2g, can be directly used for the next reaction, dry goods calculated 3-nitro The yield was 84.2percent. Melting point: 278.0 to 282.0 ° C (DSC). The purity of the product was determined by HPLC. The purity of the product was measured by HPLC. Was 98.35percent, with HPLC using a Waters XTerra MS Cl8 column (4.6 * 150 mm, particle size = 3.5 micron, UV wavelength = 210nm, intermediate retention time = 7.0 min, product retention time = 12.1 min) and Gradient elution with 0.1percent (v / v) aqueous phosphoric acid and acetonitrile as mobile phase at a flow rate of 1.0 ml / min
141.60 g
Stage #1: at 25 - 35℃;
Stage #2: at 25 - 35℃;
Stage #3: at 25℃; Reflux
In to a well cleaned and oven dried 2.OL 4neck RB flask, 97.96g of 3-aminoglutarimide hydrochloride and 500.Oml of Acetic acid were charged. Reaction mass was stirred for 5-10mm at 25-35°C. 100.Og of 4-nitrophthalic anhydride was charged in to the reaction mass.Reaction mass was stirred for 5-10mm at 25-35°C. 1 14.8g of Triethyl amine was added to the reaction mass, at 25- 35°C, in about 30-45mm. Reaction mass was maintained at 25- 35°C, for 20- 30mm. Reaction mass temperature was raised to reflux, maintained for 3.0-3.5 hours. After completion reaction, reaction mass was cooled to 25-35°C, maintained for 45-60mm. Solid reaction mass was filtered under vacuum, washing was given with 200.Oml of DM water, suck dried for 20-30mm. Wet compound is charged in to the 500.Oml 4neck RB flask, 460.Oml of DM water was charged in to the flask. Reaction mass was stirred for 20-30mm, at 25-35°C.Solid reaction mass was filtered under vacuum, washing was given with 200.Oml of DM Water, suck dried for 45-60min.Wet compound was dried in a vacuum oven, at 60-65°C, for 3-4hours, under vacuum. (68OmmJHg).Yield: 141.6.Og
Reference: [1] Patent: CN103804350, 2016, B, . Location in patent: Paragraph 0030
[2] Patent: WO2017/221261, 2017, A1, . Location in patent: Page/Page column 5
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YieldReaction ConditionsOperation in experiment
75% for 4.5 h; Reflux; Inert atmosphere 1.
2-(2,6-Dioxopiperidine-3-yl)-4-nitrophthalimide (7)
A mixture of 3-nitrophthalic anhydride (6) (1.5 g, 7.8 mmol) and (2,6-dioxopiperidine-3-yl)amine trifluoroacetate (1.9 g, 7.8 mmol) in acetic acid (60.0 mL) was refluxed for 4.5 h under a nitrogen atmosphere.
After removing solvent, the residues were recrystallized with ethyl acetate to afford product (7) (1.8 g, 75.0percent) as a purplish solid.
66.4% for 6 h; Reflux 4-Nitro-2-benzofuran -1,3-dione (7) (280.0 g, 1.4 mmol) andAcONa (177.0 mg, 2.1 mmol) were added to a solution of 3-aminopiperidine-2,6-dione trifluoroacetate (8) (350.0 g, 1.4 mmol) in aceticacid (30 mL) and the reaction mixture was stirred at refluxing for 6 h.After the mixture was cooled to room temperature, gray solid precipitated,which was filtered out and washed with water to give compound9 (Yield: 290.0 mg, 66.4percent). ESI-MS: calcd m/z=303.05, found[M+H]+=304.05, [M+Na]+=326.03 and [M+K]+=342.00.
Reference: [1] Patent: US2013/143922, 2013, A1, . Location in patent: Paragraph 0089
[2] Bioorganic Chemistry, 2018, vol. 81, p. 536 - 544
[3] Patent: WO2017/59062, 2017, A1, . Location in patent: Sheet 1
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Reference: [1] Patent: US9365640, 2016, B2, . Location in patent: Page/Page column 66
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  • [ 19171-18-7 ]
Reference: [1] ChemMedChem, 2018, vol. 13, # 15, p. 1508 - 1512
[2] ACS Chemical Biology, 2018, vol. 13, # 9, p. 2771 - 2782
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Reference: [1] Patent: CN107365295, 2017, A,
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  • [ 2353-44-8 ]
  • [ 19171-18-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 3, p. 878 - 881
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  • [ 603-81-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 8, p. 2641 - 2649
[2] Patent: US2011/269766, 2011, A1,
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937
[4] Patent: US6358978, 2002, B1,
  • 18
  • [ 641-70-3 ]
  • [ 652-39-1 ]
Reference: [1] Synthetic Communications, 1985, vol. 15, # 6, p. 485 - 490
[2] Patent: CN108558804, 2018, A, . Location in patent: Paragraph 0016; 0023; 0024; 0025
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  • [ 67-56-1 ]
  • [ 641-70-3 ]
  • [ 21606-04-2 ]
Reference: [1] Chemische Berichte, 1902, vol. 35, p. 3877,3879
[2] Journal of the Chemical Society, 1901, vol. 79, p. 1137
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 6, p. 473 - 486
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  • [ 6744-85-0 ]
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Reference: [1] Chemische Berichte, 1902, vol. 35, p. 3877,3879
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  • [ 57113-91-4 ]
Reference: [1] Patent: EP1452528, 2004, A1,
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  • [ 34529-06-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 60, p. 48861 - 48867
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  • [ 107582-20-7 ]
Reference: [1] Patent: EP1452528, 2004, A1,
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  • [ 37619-25-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937
  • 25
  • [ 641-70-3 ]
  • [ 19171-19-8 ]
Reference: [1] Patent: US2013/143922, 2013, A1,
[2] Synthetic Communications, 2016, vol. 46, # 16, p. 1343 - 1348
[3] Synthetic Communications, 2016, vol. 46, # 16, p. 1343 - 1348
[4] Patent: CN103724323, 2016, B,
[5] Patent: CN103724323, 2016, B,
[6] Patent: CN103724323, 2016, B,
[7] Patent: CN103724323, 2016, B,
[8] Patent: CN107365295, 2017, A,
[9] ACS Chemical Biology, 2018, vol. 13, # 9, p. 2771 - 2782
[10] Bioorganic Chemistry, 2018, vol. 81, p. 536 - 544
  • 26
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  • [ 711007-44-2 ]
Reference: [1] Organic Process Research and Development, 2007, vol. 11, # 4, p. 693 - 698
[2] Organic Process Research and Development, 2007, vol. 11, # 4, p. 693 - 698
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