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CAS No. :626-34-6 MDL No. :MFCD02730138
Formula : C6H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YPMPTULBFPFSEQ-PLNGDYQASA-N
M.W : 129.16 Pubchem ID :643756
Synonyms :

Safety of [ 626-34-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 626-34-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 626-34-6 ]
  • Downstream synthetic route of [ 626-34-6 ]

[ 626-34-6 ] Synthesis Path-Upstream   1~53

  • 1
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Reference: [1] Patent: US4329349, 1982, A,
  • 2
  • [ 626-34-6 ]
  • [ 107-18-6 ]
  • [ 1721-26-2 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 72, p. 7926 - 7928
  • 3
  • [ 626-34-6 ]
  • [ 1721-26-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 9, p. 1841 - 1849
[2] Chemische Berichte, 1957, vol. 90, p. 2265,2270
  • 4
  • [ 626-34-6 ]
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  • [ 1721-26-2 ]
Reference: [1] Journal of Organic Chemistry, 1956, vol. 21, p. 800
[2] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1315 - 1324
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 7, p. 1501 - 1505
  • 5
  • [ 624-67-9 ]
  • [ 626-34-6 ]
  • [ 1721-26-2 ]
Reference: [1] Archiv der Pharmazie, 1983, vol. 316, # 10, p. 879 - 887
  • 6
  • [ 5444-80-4 ]
  • [ 626-34-6 ]
  • [ 1721-26-2 ]
Reference: [1] Chemische Berichte, 1949, vol. 82, p. 216
[2] Chemische Berichte, 1939, vol. 72, p. 563,566
[3] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 897 - 900
[4] Chemische Berichte, 1949, vol. 82, p. 216
[5] Chemische Berichte, 1939, vol. 72, p. 563,566
  • 7
  • [ 626-34-6 ]
  • [ 609-08-5 ]
  • [ 4664-13-5 ]
Reference: [1] Patent: WO2010/130034, 2010, A1, . Location in patent: Page/Page column 45
  • 8
  • [ 18424-77-6 ]
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  • [ 4664-13-5 ]
Reference: [1] Helvetica Chimica Acta, 1942, vol. 25, p. 1306,1312
  • 9
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  • [ 626-34-6 ]
  • [ 609-08-5 ]
  • [ 4664-13-5 ]
Reference: [1] Helvetica Chimica Acta, 1942, vol. 25, p. 1306,1312
  • 10
  • [ 626-34-6 ]
  • [ 37669-78-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 9, p. 1841 - 1849
[2] Journal of Organic Chemistry, 1956, vol. 21, p. 800
  • 11
  • [ 626-34-6 ]
  • [ 33259-21-1 ]
Reference: [1] Journal of the Chemical Society, 1895, vol. 67, p. 222
[2] Justus Liebigs Annalen der Chemie, 1884, vol. 226, p. 310,312[3] Journal of the Chemical Society, 1891, vol. 59, p. 176
[4] Justus Liebigs Annalen der Chemie, 1909, vol. 366, p. 405
[5] Chemische Berichte, 1902, vol. 35, p. 3158
  • 12
  • [ 626-34-6 ]
  • [ 7210-76-6 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 35, p. 6439 - 6442
[2] Tetrahedron Letters, 1999, vol. 40, # 35, p. 6439 - 6442
  • 13
  • [ 626-34-6 ]
  • [ 5408-04-8 ]
  • [ 5434-29-7 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1886, vol. 236, p. 296,298[2] Chemische Berichte, 1889, vol. 22, p. 162
  • 14
  • [ 609-32-5 ]
  • [ 626-34-6 ]
  • [ 51984-71-5 ]
YieldReaction ConditionsOperation in experiment
30% With acetic acid In ethanol; water at 50℃; Compound D2 (416g, 3.6mol) and D3 (339g, 2.6mol) were added to a mixture of ethanol (1.9L), water (1.9L) and glacial acetic acid (24OmL). The resulting mixture was stirred at 500C overnight, then concentrated under vacuo. The residue was dissolved in DCM (5.0L) and filtered. The filtrate was concentrated and the residue was purified by column chromatography (EA : PE=I : 10) to provide compound D4 (165g, 30percentyield) as white solid. IH NMR (CDC13, 300MHz): 6=1.23-1.26 (t, 3H), 2.25 (s, 3H), 4.14-4.21 (q, 2H), 8.91-8.92 (t, IH), 9.37-9.38 (d, IH). LC-MS [M+l]+ : 210.2.
Reference: [1] Patent: WO2008/88881, 2008, A1, . Location in patent: Page/Page column 33-34
  • 15
  • [ 34461-00-2 ]
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  • [ 51984-71-5 ]
Reference: [1] Patent: WO2007/56016, 2007, A2, . Location in patent: Page/Page column 105
  • 16
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  • [ 51984-71-5 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 737
  • 17
  • [ 626-34-6 ]
  • [ 105-53-3 ]
  • [ 10350-10-4 ]
YieldReaction ConditionsOperation in experiment
81.85% With sodium ethanolate In ethanol at 80 - 90℃; for 24 h; Ethyl 3-aminocrotonate (100 g, 0.7752 mol) was added to the reactor,(124 g, 0.7752 mol) of sodium ethoxide (65 g, 0.9559 mol) and absolute ethanol (240 g)Then the system slowly heated to 80 ~ 90 ,The system was in the reflux state,The reaction was stirred at the same temperature for 24 hours.The system was cooled to 50 ~ 60 ,100 g of ethanol was concentrated under reduced pressure,The concentrated solution was slowly added to 1000 ml of water,Adding 10g of basic activated carbon,After 1 hour, filter.The filtrate was cooled down to a temperature below 0 ° C,Adjust the system with ammonium chloride pH = 2 ~ 3,A large number of solid precipitation filter,filter,The solid is then dried at a temperature of 50 to 60 ° C,White needle-like crystals is 2,4-dihydroxy-6-methyl-nicotinic acid ethyl ester,W = 125 g (Yield = 81.85percent, HPLC = 99.5percent),
Reference: [1] Patent: CN106279011, 2017, A, . Location in patent: Paragraph 0021; 0022
[2] Chemische Berichte, 1898, vol. 31, p. 766,769[3] Chemische Berichte, 1898, vol. 31, p. 765
  • 18
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YieldReaction ConditionsOperation in experiment
94% With ammonia In water Example 9: Process for the preparation of Ethyl amino crotonate Continuous flow experiment was carried out in a SS316 tubular reactor of 1.58 mm o.d. by mixing ethyl acetoacetate with aqueous ammonia (25percent solution) in the ratio 1:3 using a simple T-mixer and reactor with 1 m length having a residence time of 22 min. Product yields was 94percent at 50 Q C.
89% With ammonium acetate; acetic acid In toluene at 140℃; for 0.333333 h; Molecular sieve; Sealed tube General procedure: b-keto esters 5 a-n (1.0 equiv.), Ammonium acetate (3.0 equiv.)and Acetic acid (drops) were dissolved in dry Toluol (6 mL) in a10 mL reaction glass vial containing a tiny stirring magnet andmolecular sieves. The vial was sealed tightly with an aluminium-Teflon® crimp top and the mixture was irradiated for 20 min at apre-selected temperature of 140 °C, with an irradiation power of60W. After the reaction, the vial was cooled to 50 °C by gas jetcooling. The crude mixture was portioned between ethyl acetateand saturated solution of Sodium bicarbonate (15 mL of each) andthe aqueous layer was extracted with ethyl acetate (3 15 mL). Thecombined organic layer were dried on Sodium sulfate anhydrous,filtered and the solvent was removed under reduce pressure. Then,final crude compounds were purified by flash chromatography oversilica gel.4.5.1. Ethyl 3-aminobut-2-enoate (6a)Compound 6a was synthesized from Ethyl 3-(2-fluorophenyl)-3-oxopropanoate 5a(1.0equiv.), Ammonium acetate (4.0equiv.) andacetic acid (7 drops). Flash chromatography with hexane/EtOAc(80:20 to 70:30) afforded analytically pure product as 89percent.1H NMR (CDCl3, 300 MHz) δ (ppm) 1.24 (t, 3H, J7.36 Hz), 3.51(s, 3H), 4.09 (q, 2H, J7.28 Hz), 4.60 (s, 1H).
80% at 70 - 75℃; for 0.05 h; General procedure: 4-Amino-pent-3-en-2-one, 29 (Ref 33). A mixture of pentane-2,4-dione (5.0 mmol), ammonium salts (5.0 mmol) and bmim[HSO4] (0.7 mmol) in a 25 mL conical flask was irradiated at 70-75°C for 3 min under microwave. After completion of the reaction as indicated by TLC, the reaction mixture was extracted with dichloromethane (2 x 10 mL) and washed with brine. The organic layer was dried over anhydrous sodium sulphate. Removal of solvent under reduced pressure followed by column chromatography yielded pure product.
Reference: [1] Comptes Rendus Chimie, 2011, vol. 14, # 5, p. 511 - 515
[2] Patent: WO2012/147103, 2012, A2, . Location in patent: Page/Page column 7
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1986, vol. 35, p. 1438 - 1442[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1986, # 7, p. 1586 - 1592
[5] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 946 - 960
[6] E-Journal of Chemistry, 2010, vol. 7, # 4, p. 1546 - 1554
[7] Journal of the American Chemical Society, 2010, vol. 132, # 28, p. 9585 - 9587
[8] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 7, p. 900 - 906
[9] Journal of the Chemical Society of Pakistan, 2011, vol. 33, # 6, p. 916 - 921
[10] Chemische Berichte, 1878, vol. 11, p. 1194
[11] Justus Liebigs Annalen der Chemie, 1882, vol. 213, p. 171
[12] Bulletin de la Societe Chimique de France, 1945, vol. <5> 12, p. 161,166
[13] Justus Liebigs Annalen der Chemie, 1884, vol. 226, p. 310,312[14] Journal of the Chemical Society, 1891, vol. 59, p. 176
[15] Annales de Chimie (Cachan, France), 1932, vol. <10> 18, p. 133[16] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1930, vol. 190, p. 269
[17] Journal of Organic Chemistry, 1949, vol. 14, p. 802,809
[18] Bulletin de la Societe Chimique de France, 1945, vol. <5> 12, p. 161,166
[19] Justus Liebigs Annalen der Chemie, 1909, vol. 366, p. 405
[20] Annales de Chimie (Cachan, France), 1932, vol. <10> 18, p. 133[21] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1930, vol. 190, p. 269
[22] Arzneimittel-Forschung/Drug Research, 1981, vol. 31, # 3, p. 407 - 409
[23] Journal of Organic Chemistry, 1999, vol. 64, # 18, p. 6907 - 6910
[24] Synlett, 2001, # 7, p. 1149 - 1151
[25] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 3, p. 461 - 464
[26] Journal of the American Chemical Society, 2002, vol. 124, # 49, p. 14552 - 14553
[27] Organic letters, 2002, vol. 4, # 14, p. 2429 - 2431
[28] Synthetic Communications, 2006, vol. 36, # 24, p. 3693 - 3702
[29] Bulletin de la Societe Chimique de France, 1895, vol. <3> 13, p. 71
[30] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 20, p. 9349 - 9358
[31] European Journal of Organic Chemistry, 2008, # 19, p. 3352 - 3362
[32] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1579 - 1586
[33] Molecules, 2010, vol. 15, # 5, p. 3211 - 3227
[34] Organic Letters, 2011, vol. 13, # 7, p. 1754 - 1757
[35] Organic Process Research and Development, 2007, vol. 11, # 3, p. 568 - 577
[36] Advanced Synthesis and Catalysis, 2014, vol. 356, # 5, p. 1113 - 1118
[37] Archives of Pharmacal Research, 2013, vol. 36, # 11, p. 1392 - 1402
[38] European Journal of Pharmacology, 2015, vol. 746, p. 233 - 244
[39] Turkish Journal of Chemistry, 2015, vol. 39, # 4, p. 843 - 849
[40] RSC Advances, 2016, vol. 6, # 45, p. 39433 - 39443
[41] Advanced Synthesis and Catalysis, 2017, vol. 359, # 6, p. 952 - 958
[42] Angewandte Chemie - International Edition, 2017, vol. 56, # 15, p. 4277 - 4281[43] Angew. Chem., 2017, vol. 129, p. 4341 - 4345,5
[44] Organic Letters, 2017, vol. 19, # 19, p. 5130 - 5133
  • 19
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  • [ 123-11-5 ]
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Reference: [1] Comptes Rendus Chimie, 2011, vol. 14, # 5, p. 511 - 515
  • 20
  • [ 105-36-2 ]
  • [ 75-05-8 ]
  • [ 626-34-6 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 72, p. 7926 - 7928
[2] European Journal of Organic Chemistry, 2018, vol. 2018, # 5, p. 666 - 672
  • 21
  • [ 128001-87-6 ]
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  • [ 127983-58-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1807 - 1810
  • 22
  • [ 6127-92-0 ]
  • [ 626-34-6 ]
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  • 23
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 40, p. 12808 - 12816
  • 24
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  • [ 67-68-5 ]
  • [ 1149-24-2 ]
  • [ 626-34-6 ]
Reference: [1] Chinese Journal of Chemistry, 2016, vol. 34, # 9, p. 887 - 894
  • 25
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  • [ 626-34-6 ]
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[3] Justus Liebigs Annalen der Chemie, 1906, vol. 345, p. 96[4] Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 52,56, 58
  • 26
  • [ 64-17-5 ]
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  • 27
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  • [ 141-97-9 ]
  • [ 100-52-7 ]
  • [ 626-34-6 ]
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  • 28
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  • [ 7664-41-7 ]
  • [ 626-34-6 ]
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  • 29
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Reference: [1] Justus Liebigs Annalen der Chemie, 1906, vol. 345, p. 96[2] Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 52,56, 58
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Reference: [1] Journal of the Chemical Society, 1922, vol. 121, p. 2227
  • 32
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  • [ 60-34-4 ]
  • [ 2749-59-9 ]
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[2] Anales de Quimica, 1995, vol. 91, # 3-4, p. 284 - 289
  • 33
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  • [ 68-12-2 ]
  • [ 15901-51-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1978, vol. 15, p. 1001 - 1003
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YieldReaction ConditionsOperation in experiment
66% at 90℃; for 0.0166667 h; Sealed tube; Microwave irradiation; Green chemistry To a 10 mL Pyrex pressure vial for closed vessel formicrowave heating reaction, was added 0.5 mmol of theenaminone 6a and 0.1 mL of acetic anhydride. The mixturewas subjected to heating in a CEM Discover SP reactorat 90 °C and 200 W for 1 minute, with IR temperaturecontrol and medium stirring speed using cylindrical stirbars (10 × 3 mm), default ramp time of 10 min. After thistime, the mixture was cooled to room temperature and then4 mL of distilled water was added. After cooling in therefrigerator the solid product was filtered and washed withcold water, resulting in 56.6 mg of white crystals of 9, 66percentyield; m.p. 61.8-62.2 °C (Lit31 63-65 °C); IR (KBr) n / cm-13224, 3074, 2978, 2929, 1712, 1639, 1500, 1475, 1440,1385, 1274, 1288, 1176, 1064, 1029, 983, 839, 783, 663,605; 1H NMR (500 MHz, CDCl3) d 4.87 (d, J 1.0 Hz, NH),4.14 (q, 2H, J 7.0 Hz, CH2), 2.36 (d, 3H, J 1.0 Hz, CH3),2.12 (s, 3H, CH3), 1.26 (t, J 7.0 Hz, 3H, CH3); 13C NMR(125 MHz, CDCl3) d 14.2, 21.8, 25.2, 59.8, 96.4, 155.0,168.9, 169.2.
Reference: [1] Journal of the Brazilian Chemical Society, 2017, vol. 28, # 6, p. 1137 - 1144
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Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 18, p. 6907 - 6910
[2] Journal of the American Chemical Society, 2002, vol. 124, # 49, p. 14552 - 14553
[3] Organic letters, 2002, vol. 4, # 14, p. 2429 - 2431
[4] Journal of the American Chemical Society, 2010, vol. 132, # 28, p. 9585 - 9587
[5] Organic Letters, 2011, vol. 13, # 7, p. 1754 - 1757
  • 36
  • [ 108-24-7 ]
  • [ 626-34-6 ]
  • [ 23652-67-7 ]
Reference: [1] European Journal of Organic Chemistry, 2008, # 19, p. 3352 - 3362
[2] Organic Process Research and Development, 2007, vol. 11, # 3, p. 568 - 577
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Reference: [1] Bulletin des Societes Chimiques Belges, 1981, vol. 90, # 1, p. 75 - 82
  • 38
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  • [ 75-36-5 ]
  • [ 23652-67-7 ]
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Reference: [1] Helvetica Chimica Acta, 1950, vol. 33, p. 1787,1795
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  • [ 23652-67-7 ]
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  • [ 78120-37-3 ]
Reference: [1] Helvetica Chimica Acta, 1950, vol. 33, p. 1787,1795
  • 40
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  • [ 2867-59-6 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 18, p. 5328 - 5335
  • 41
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  • [ 2867-59-6 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 37, p. 7852 - 7858
  • 42
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  • [ 626-34-6 ]
  • [ 620-80-4 ]
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[2] Chemische Berichte, 1898, vol. 31, p. 734
  • 43
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YieldReaction ConditionsOperation in experiment
94.3%
Stage #1: With piperidine; pyridine In neat (no solvent) at 75 - 80℃; for 9 h;
Stage #2: for 1 h; Reflux
20.0-dichlorobenzaldehyde 70.0 g (0.40 mol), β-aminocrotonate ethyl ester in a 500 mL round bottom flask55.8g (0.48mol),62.0 g (0.48 mol) of methyl acetoacetate, followed by 4.5 g (0.053 mol) of piperidine and 4.2 g (0.053 mol) of pyridine.The heating was started slowly and the temperature was raised. The reaction was maintained at 75-80 ° C for 9 h, and 200 g of absolute ethanol was added while heating, and the mixture was heated to reflux for 1 h, and filtered while hot.The mixture was cooled to 15 ° C and stirred for 1 h, and suction filtered. The filter cake was washed with a small amount of dry ethanol and dried to give 145 g of pale yellow solid.Yield: 94.3percent, purity 99.1percent
Reference: [1] Patent: CN108840819, 2018, A, . Location in patent: Paragraph 0014; 0040-0042; 0045-0048; 0051-0053
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Reference: [1] Patent: US5977369, 1999, A,
  • 45
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Reference: [1] Applied Catalysis A: General, 2017, vol. 530, p. 203 - 210
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  • [ 72509-76-3 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 52, p. 10222 - 10228
  • 47
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  • [ 68064-69-7 ]
  • [ 72509-76-3 ]
Reference: [1] Patent: WO2012/123966, 2012, A1, . Location in patent: Page/Page column 29
  • 48
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  • [ 643-79-8 ]
  • [ 103890-78-4 ]
YieldReaction ConditionsOperation in experiment
40.9%
Stage #1: With sodium hydroxide In dichloromethane; water at -5 - -3℃; for 2.75 h; Industry scale
Stage #2: With trifluoroacetic acid In isopropyl alcohol at -7℃; for 2.75 h;
Stage #3: With sodium hydrogencarbonate In water; ethyl acetate; isopropyl alcohol at 0 - 25℃; for 0.333333 h;
18 liters of dichloromethane was taken into a reactor and 5 kg of tertiary-butoxy carbonyl methyl triphenyl phosphonium bromide (obtained using a similar process as described in Example 1) was added to it. 2.05 kg of ortho-phtalaldehyde was added to the reaction mass and another 1 liter of dichloromethane was added to it. The reaction mass was stirred for about 15 minutes and then cooled to about -5° C. A solution of 2.65 kg of sodium hydroxide flakes in 5 liters of water at about 25° C. was added to the reaction mass at -3° C. and maintained at -3° C. for 2.5 hours. Reaction completion was checked using thin layer chromatography. After the reaction was completed, the temperature of the reaction mass was raised to 25° C. and stirred for 30 minutes. The organic layer was separated from the reaction mass and distilled without vacuum at a temperature of 52° C. The residue obtained was maintained at 52° C. for 15 minutes. 35 liters of n-heptane was added to the reaction mass at 52° C. 4 liters of the n-heptane was distilled off from the reaction mass under a vacuum of 500 mm Hg at 63° C. The reaction mass was then cooled to 35° C. and maintained for 1.5 hours. The reaction mass was then filtered under vacuum to remove the undissolved material. The filtered cake was washed with 7.5 liters of n-heptane. The filtrate was taken into another reactor and the solvent was distilled off completely under a vacuum of 610 mm Hg and at 68° C. The reaction mass was then cooled to 33° C. and 11.5 liters of isopropanol was charged into it. The reaction mass was then cooled to -7° C. A solution of 4.25 kg of ethyl-3-aminocrotonate in 12.5 liters of isopropanol was added to the reaction mass at -7° C. 2.8 liters of trifluoroacetic acid was added to the reaction mass at -7° C. followed by addition of 1 liter of isopropanol. The reaction mass was maintained at -7° C. for 2 hours 45 minutes. Reaction completion was checked using thin layer chromatography. A solution of 2.6 kg of sodium bicarbonate in 50 liters of water was added to the reaction mass 0° C. and 25 liters of ethyl acetate was added to it. The temperature of the reaction mass was heated to 25° C. and stirred for 20 minutes. The aqueous layer was separated and extracted with 12.5 liters of ethyl acetate. The combined organic layer was taken into a separate reactor and the solvent was distilled off atmospherically at 81° C. The residue was distilled off completely, and then 5 liters of isopropanol was added to it. The reaction mass was distilled off completely and again 5 liters of isopropanol was added to the residue obtained. The reaction mass was again distilled off completely and finally the residue was dissolved in 63 liters of isopropanol by heating to 85° C. to get clear dissolution. The reaction mass was then cooled to 2° C. and maintained for 1.5 hours. The isolated material was filtered and washed with 2.5 liters of isopropanol. The wet material was dried at 50° C. for 30 minutes. The dry material was taken into another reactor and 23 liters of isopropanol was added to it. The reaction mass was heated to 65° C. and maintained for 30 minutes. The reaction mass was then cooled to 2° C. and maintained for 1 hour. The reaction mass was filtered and washed with 1.5 liters of isopropanol. The wet solid was dried at a temperature of 60° C. and a vacuum of 630 mm Hg for 5 hours to yield 2.04 kg (yield: 40.9percent) of the title compound. Triphenyl phosphine oxide content: less than 0.0011 area-percent.
Reference: [1] Patent: US2007/43088, 2007, A1, . Location in patent: Page/Page column 6
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  • [ 643-79-8 ]
  • [ 103890-78-4 ]
YieldReaction ConditionsOperation in experiment
82.45%
Stage #1: for 0.666667 h; Cooling with ice
Stage #2: With ammonium sulfate In ethanol; dichloromethane for 1.5 h; Cooling with ice
52.4 g of triphenylphosphine and 45.0 g of tert-butyl chloroacetate,Set microwave reactor, added toluene 200g, titanium dioxide 1g,Select the microwave frequency of 2450MHz, heating to 105 ~ 110 ,The reaction for 1 hour, cooled, filtered, the filter cake was washed with an appropriate amount of isopropyl ether,Dried to give a white solid, add water 100g, stirred for 10 minutes,Sodium hydroxide solution was added dropwise, filtered and dried to give a white solid,Add methylene chloride, madeTert-butyl triphenylphosphinoacetate dichloromethane solution;5.0 g of o-phthalaldehyde was added to 50 g of methylene chloride, and in an ice-salt bath,Tert-butyl triphenylphosphinyl acetate methylene chloride solution, the reaction 40 minutes,The methylene chloride was distilled off, the filter cake was washed with an appropriate amount of isopropyl ether,Isopropyl ether evaporated to give a yellow oil, addedEthyl aminocrotonate 12g,Ammonium sulfate 1g, dissolved in an appropriate amount of anhydrous ethanol, ice-salt bath,The reaction 1.5 hours, the reaction was added aqueous sodium bicarbonate,Get tan solid, filtered, dried, set ultrasound reactor,Add 200g of ethyl acetate, heat to dissolve, filter hotly,Select ultrasonic frequency 15kHz, cooling, precipitation of crystals, suction filtration,Dry, doxepin dihydrate crystals, yield 82.45percent.
Reference: [1] Patent: CN106892862, 2017, A, . Location in patent: Paragraph 0016
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  • [ 103890-69-3 ]
  • [ 144-55-8 ]
  • [ 626-34-6 ]
  • [ 103890-78-4 ]
Reference: [1] Patent: US4801599, 1989, A,
  • 51
  • [ 626-34-6 ]
  • [ 122-51-0 ]
  • [ 110960-73-1 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 10, p. 2161 - 2164
  • 52
  • [ 626-34-6 ]
  • [ 686279-09-4 ]
Reference: [1] Patent: WO2012/97683, 2012, A1,
[2] Patent: US2014/171429, 2014, A1,
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  • [ 626-34-6 ]
  • [ 686279-09-4 ]
Reference: [1] Patent: WO2012/97682, 2012, A1,
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