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[ CAS No. 58259-34-0 ]

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Chemical Structure| 58259-34-0
Chemical Structure| 58259-34-0
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CAS No. :58259-34-0 MDL No. :MFCD00024635
Formula : C10H14N2O2 Boiling Point : 328.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :194.23 g/mol Pubchem ID :3801140
Synonyms :

Safety of [ 58259-34-0 ]

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

Application In Synthesis of [ 58259-34-0 ]

  • Upstream synthesis route of [ 58259-34-0 ]
  • Downstream synthetic route of [ 58259-34-0 ]

[ 58259-34-0 ] Synthesis Path-Upstream   1~21

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YieldReaction ConditionsOperation in experiment
80% With copper(l) iodide; C12H13N3O; potassium carbonate In diethylene glycol at 10℃; for 12 h; Sealed tube The 201 mg (1mmol) 4 - nitro-bromophenylacetic, 110 mg (1.5mmol) n-butylamine, 4.8 mg (0.025mmol) CuI, 10.8 mg (0.05mmol) ligand L2, 552mg (4mmol) K2CO3, 2 ml DEG, adding 10 ml reaction tube, sealing, 10 °C reaction under the condition 12h. After the stop of the reaction, water, extracted with ethyl acetate, washing, saturated salt water washing, after drying with anhydrous sodium sulfate, filtered, the filtrate is distilled under reduced pressure, purification by silica gel chromatography separation column column, shall be N - n-butylamine -4 - nitroaniline 155 mg, yield 80percent.
51% With copper(l) iodide; tetrabutylammomium bromide; potassium hydroxide In water at 90℃; for 16 h; Green chemistry General procedure: A 10 mL of vial was charged with CuI (10 mg, 0.05 mmol), PSP (0.25 mmol, size less than 90 μM), TBAB (40 mg, 0.25 mmol), base (1.0 mmol), aryl halides (0.5 mmol), arylamine (2.0 mmol), H2O (1.0 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into an oil bath, which was preheated to 70 °C (90 °C for alkyl amine, 120 °C for imidazole). The reaction mixture was stirred for another 16 h (8 h for imidazole). After allowing the mixture to cool to room temperature, the reaction mixture was filtrated, the precipitates were washed with water and ethyl acetate thoroughly. The filtrate was extracted with ethyl acetate (3×25 mL). The combined organic phases was washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel to afford the desired products.
15% With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In tetrahydrofuran at 80℃; for 12 h; Inert atmosphere To the mixture of butylamine (0.524 mmol) and t-BuONa (0.75 mmol) in anhydrous THF (3 mL) was added 4-bromo-1-nitrobenzene (0.49 mmol), Pd(dba)2 (0.02 mmol) and BINAP (0.02 mmol) in 2 mL THF under Ar. The mixture was degassed via freeze-thaw and finally, the reaction was carried out at 80 oC. After 12 h, the solution was cooled down to ambient temperature and the solvent was removed in vacuo. The residue was purified via flash chromatography to yield the product (yield 15percent): IR (neat) 3317, 3085, 1586, 1537 cm-1; 1H NMR (400 MHz, CDCl3): δ 8.1-7.8 (m, 2H), 7.6-7.4 (m, 2H), 3.0-2.8 (m, 2H), 2.1-0.9 (m, 7H); HRMS m/z: found 193.71, calculated 194.105.
Reference: [1] Patent: CN106883132, 2017, A, . Location in patent: Paragraph 0075-0077
[2] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5416 - 5423
[3] Tetrahedron, 2013, vol. 69, # 42, p. 8974 - 8977
[4] Tetrahedron Letters, 2013, vol. 54, # 48, p. 6665 - 6668
  • 2
  • [ 54191-12-7 ]
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YieldReaction ConditionsOperation in experiment
72% With borane-THF In tetrahydrofuran at 20℃; for 2 h; To a solution of 56 (2.95 g, 14.2 mmol) in tetrahydrofuran (10 mL) was added borane–tetrahydrofuran complex (1 M in tetrahydrofuran, 18.0 mL) at ambient temperature. After stirring for2 h at this temperature, the reaction mixture was quenched with addition of methanol and water. Themixture was concentrated in vacuo and diluted with ethyl acetate. The organic layer was washed withwater and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified withsilica gel column chromatography (n-hexane/ethyl acetate = 5:1) to afford the title compound (1.98 g,10.2 mmol, 72percent) as a yellow solid.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2781 - 2787
[2] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1985, p. 1963 - 1968
  • 3
  • [ 636-98-6 ]
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YieldReaction ConditionsOperation in experiment
6 %Spectr. With copper(I) oxide In acetonitrile for 6 h; Reflux General procedure: In a 10 mL flask were placed aryl halide (0.5 mmol), diamine (1.0; 2.0 or 3.7 mmol), copper catalyst (0.5; 1.0 or 10 mol percent), and acetonitrile (2–3 mL). The reaction was then kept under stirring and reflux. After the reaction was complete (TLC), the resulting mixture was diluted with brine (2–3 mL) and extracted with ethyl acetate (4 Χ 7 mL). Then the organic phase was dried over anhydrous sodium sulfate, filtered under Celite, and the solvent was eliminated by vacuum. The crude product was then analyzed by 1H NMR. When necessary, the mixture was purified by column chromatography on silica gel or by thin layer chromatography plates with UV 254 nm to afford the desired product.
Reference: [1] Tetrahedron, 2008, vol. 64, # 49, p. 11230 - 11236
[2] ChemCatChem, 2016, vol. 8, # 7, p. 1319 - 1328
[3] Synlett, 2011, # 13, p. 1859 - 1862
[4] Journal of Organic Chemistry, 2011, vol. 76, # 3, p. 800 - 810
[5] Organic Letters, 2003, vol. 5, # 26, p. 4987 - 4990
[6] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5416 - 5423
[7] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 1, p. 42 - 49
[8] Tetrahedron Letters, 2013, vol. 54, # 19, p. 2332 - 2335
  • 4
  • [ 100-02-7 ]
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YieldReaction ConditionsOperation in experiment
64% at 120℃; for 9 h; Inert atmosphere P-nitrophenol (209 mg, 1.5 mmol)Was dissolved in N, N-dimethylformamide (2 mL)To this was added n-butylamine (2.9 mL, 30 mmol)120 ° C,Nitrogen reaction conditions for 9 hours,Cool to room temperature.The reaction solution was poured into 16 mL of water and extracted with dichloromethane (3 x 5 mL). The organic phase was washed with saturated brine (2 x 4 mL), dried over anhydrous sodium sulfate, filtered, sintered, and rapidly purified by silica gel column chromatography The product is dichloromethane: methanol = 100: 1 V / V) to give the product N-n-butyl-4-nitroaniline,Yellow liquid,The yield was 64percent.
Reference: [1] Patent: CN106631820, 2017, A, . Location in patent: Paragraph 0035; 0036; 0037; 0038
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  • [ 100-00-5 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 1, p. 42 - 49
[2] Chemistry Letters, 1987, p. 1187 - 1190
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  • [ 100-01-6 ]
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Reference: [1] Catalysis Letters, 2011, vol. 141, # 1, p. 178 - 182
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 22, p. 3824 - 3835
  • 7
  • [ 21724-51-6 ]
  • [ 98-95-3 ]
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Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 17, p. 3978 - 3982
  • 8
  • [ 14150-94-8 ]
  • [ 109-73-9 ]
  • [ 67-64-1 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 7, p. 2174 - 2180
  • 9
  • [ 123-72-8 ]
  • [ 100-01-6 ]
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Reference: [1] Synthesis, 1993, # 1, p. 121 - 125
  • 10
  • [ 15676-66-1 ]
  • [ 4482-01-3 ]
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Reference: [1] European Journal of Organic Chemistry, 2008, # 5, p. 862 - 868
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  • [ 1516-60-5 ]
  • [ 60669-69-4 ]
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Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 17, p. 7017 - 7026
  • 12
  • [ 109-73-9 ]
  • [ 350-46-9 ]
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Reference: [1] Journal of Materials Chemistry, 1999, vol. 9, # 8, p. 1699 - 1705
[2] Bulletin de la Societe Chimique de France, 1956, p. 311,315
[3] New Journal of Chemistry, 2012, vol. 36, # 7, p. 1519 - 1526
  • 13
  • [ 56269-49-9 ]
  • [ 58259-34-0 ]
  • [ 100-15-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 828 - 832
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 828 - 832
  • 14
  • [ 98-95-3 ]
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Reference: [1] European Journal of Organic Chemistry, 2009, # 4, p. 564 - 574
  • 15
  • [ 109-69-3 ]
  • [ 100-01-6 ]
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Reference: [1] European Journal of Organic Chemistry, 2012, # 16, p. 3105 - 3111
  • 16
  • [ 100-01-6 ]
  • [ 58259-34-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2781 - 2787
  • 17
  • [ 100-17-4 ]
  • [ 109-73-9 ]
  • [ 58259-34-0 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 37, p. 4147 - 4150
  • 18
  • [ 68906-00-3 ]
  • [ 109-73-9 ]
  • [ 67-64-1 ]
  • [ 58259-34-0 ]
Reference: [1] Russian Chemical Bulletin, 1994, vol. 43, # 6, p. 1041 - 1043[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1994, # 6, p. 1102 - 1104
  • 19
  • [ 830-03-5 ]
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Reference: [1] New Journal of Chemistry, 2012, vol. 36, # 7, p. 1519 - 1526
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  • [ 100-00-5 ]
  • [ 109-73-9 ]
  • [ 68-12-2 ]
  • [ 58259-34-0 ]
  • [ 100-23-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 403 - 404[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 2, p. 455 - 456
  • 21
  • [ 14368-49-1 ]
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  • [ 59453-65-5 ]
  • [ 59453-64-4 ]
  • [ 52010-79-4 ]
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  • [ 59453-63-3 ]
  • [ 100-00-5 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 4, p. 581 - 584
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