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[ CAS No. 4491-33-2 ]

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Chemical Structure| 4491-33-2
Chemical Structure| 4491-33-2
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Product Details of [ 4491-33-2 ]

CAS No. :4491-33-2 MDL No. :MFCD02149441
Formula : C12H11NO2 Boiling Point : 348°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :201.22 g/mol Pubchem ID :421739
Synonyms :

Safety of [ 4491-33-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4491-33-2 ]

  • Upstream synthesis route of [ 4491-33-2 ]
  • Downstream synthetic route of [ 4491-33-2 ]

[ 4491-33-2 ] Synthesis Path-Upstream   1~30

  • 1
  • [ 4491-33-2 ]
  • [ 1780-17-2 ]
Reference: [1] Chemische Berichte, 1952, vol. 85, p. 152,158
  • 2
  • [ 617-35-6 ]
  • [ 91-22-5 ]
  • [ 10447-29-7 ]
  • [ 4491-33-2 ]
  • [ 25635-39-6 ]
Reference: [1] Tetrahedron, 1986, vol. 42, # 21, p. 5973 - 5977
  • 3
  • [ 93-10-7 ]
  • [ 75-03-6 ]
  • [ 4491-33-2 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 18 h; Inert atmosphere A mixture of quinaldine acid (5) (2.0 g, 11.55 mmol), dried K2CO3 (3.19 g, 23.10 mmol) and anhydrous DMF (24 mL) was stirred until the reagents had been dissolved under an argon atmosphere. Iodoethane (2.77 mL, 34.65 mmol) was added and stirred for 18 h to 60 °C. A 30percent cooled aqueous solution of HCl (30 mL) was added. The medium was neutralized with a saturated solution of NaHCO3 until the gas formation was ceased. Extraction was carried out with ethyl acetate (3x 60 mL). The combined organic phases were washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography by eluting with hexane/AcOEt (8:2) to furnish ester 6 as a translucent oil in quantitative yield. Rf 0.51 (hexane/AcOEt 7:3). IR (neat) νmax/cm-1: 3061, 2982, 2938, 2904, 1714, 1463, 1368, 1312, 1133, 1103, 1016, 844, 774. 1H NMR (400 MHz, CDCl3) δ 7.96-7.94 (m, 1H), 7.85-7.81 (m, 1H), 7.76-7.73 (m, 1H), 7.42-7.36 (m, 2H), 7.22-7.18 (m, 1H), 4.22-4.17 (m, 2H), 1.14-1.10 (m, 3H). 13C NMR (100 MHz, CDCl3) δ 164.9, 147.9, 147.2, 136.8, 130.3, 129.8, 128.9, 128.1, 127.2, 120.6, 61.7, 14.1. HRMS (ESI+) calcd for C12H11NO2 [M+H]+ 202.0868, found 202.0868.
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 33, p. 3311 - 3315
  • 4
  • [ 93-10-7 ]
  • [ 64-17-5 ]
  • [ 4491-33-2 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 215
[2] Patent: US2008/153871, 2008, A1, . Location in patent: Page/Page column 31-32
[3] European Journal of Medicinal Chemistry, 2009, vol. 44, # 5, p. 2017 - 2029
[4] Turkish Journal of Chemistry, 2012, vol. 36, # 2, p. 233 - 246
[5] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 5, p. 1152 - 1156
  • 5
  • [ 55531-67-4 ]
  • [ 62-53-3 ]
  • [ 4491-33-2 ]
YieldReaction ConditionsOperation in experiment
66% at 80℃; for 6 h; 60.0 mg (0.3 mmol) of ethyl 4,4-diethoxy-2-butenoate obtained in the step (2) and 28.0 mg (0.3 mmol) of aniline dissolved in 1 mL of acetic acid in a reactor equipped with magnetic stirring. ,The mixture was stirred and reacted at 80 ° C for 6 h.The TCL stops the heating after detecting the reaction. The product and the starting material were separated by preparative thin layer chromatography (PTLC). The eluent was a mixture of petroleum ether and ethyl acetate in a volume ratio of 6:1.Finally, 40.0 mg (0.2 mmol) of the ethyl quinolin-2-carboxylate was obtained.
Reference: [1] Patent: CN108314647, 2018, A, . Location in patent: Paragraph 0028; 0036; 0042; 0043; 0046
  • 6
  • [ 93-10-7 ]
  • [ 4491-33-2 ]
Reference: [1] Chemische Berichte, 1936, vol. 69, p. 2799
[2] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 8, p. 2891 - 2898
[3] Patent: US5324725, 1994, A,
  • 7
  • [ 19213-72-0 ]
  • [ 93-10-7 ]
  • [ 4491-33-2 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 8, p. 1970 - 1973
  • 8
  • [ 705966-83-2 ]
  • [ 4491-33-2 ]
  • [ 50458-79-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2004, vol. 77, # 4, p. 785 - 796
  • 9
  • [ 924-44-7 ]
  • [ 52670-38-9 ]
  • [ 4491-33-2 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 3, p. 836 - 839
  • 10
  • [ 612-62-4 ]
  • [ 95-92-1 ]
  • [ 4491-33-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 15, p. 2699 - 2704
  • 11
  • [ 1015760-90-3 ]
  • [ 4491-33-2 ]
Reference: [1] Heterocycles, 2007, vol. 74, # C, p. 1015 - 1018
  • 12
  • [ 110-89-4 ]
  • [ 924-44-7 ]
  • [ 52670-38-9 ]
  • [ 4491-33-2 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 3, p. 836 - 839
  • 13
  • [ 894789-59-4 ]
  • [ 4491-33-2 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 41, p. 13433 - 13438
  • 14
  • [ 91-63-4 ]
  • [ 64-17-5 ]
  • [ 4491-33-2 ]
Reference: [1] Catalysis Science and Technology, 2016, vol. 6, # 3, p. 690 - 693
  • 15
  • [ 613-53-6 ]
  • [ 4491-33-2 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 2381,2383
  • 16
  • [ 615-43-0 ]
  • [ 4491-33-2 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 3, p. 836 - 839
  • 17
  • [ 4755-77-5 ]
  • [ 79476-04-3 ]
  • [ 4491-33-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 6, p. 1028 - 1030
  • 18
  • [ 5470-96-2 ]
  • [ 64-17-5 ]
  • [ 4491-33-2 ]
Reference: [1] Chemistry Letters, 2009, vol. 38, # 5, p. 484 - 485
  • 19
  • [ 612-62-4 ]
  • [ 75-00-3 ]
  • [ 124-38-9 ]
  • [ 91-22-5 ]
  • [ 4491-33-2 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1981, vol. 35, # 3, p. 185 - 192
  • 20
  • [ 1613-37-2 ]
  • [ 4491-33-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 8, p. 2891 - 2898
  • 21
  • [ 1436-43-7 ]
  • [ 4491-33-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 8, p. 2891 - 2898
  • 22
  • [ 91-22-5 ]
  • [ 4491-33-2 ]
  • [ 119-91-5 ]
Reference: [1] Pharmazie, 1990, vol. 45, # 12, p. 900 - 904
  • 23
  • [ 612-62-4 ]
  • [ 91-22-5 ]
  • [ 4491-33-2 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1981, vol. 35, # 3, p. 185 - 192
  • 24
  • [ 50342-01-3 ]
  • [ 64-17-5 ]
  • [ 4491-33-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 8, p. 2891 - 2898
  • 25
  • [ 91-22-5 ]
  • [ 75-00-3 ]
  • [ 124-38-9 ]
  • [ 4491-33-2 ]
  • [ 119-91-5 ]
Reference: [1] Pharmazie, 1990, vol. 45, # 12, p. 900 - 904
  • 26
  • [ 1436-43-7 ]
  • [ 5382-42-3 ]
  • [ 4491-33-2 ]
Reference: [1] Yakugaku Zasshi, 1959, vol. 79, p. 702[2] Chem.Abstr., 1959, p. 21999
  • 27
  • [ 617-35-6 ]
  • [ 91-22-5 ]
  • [ 10447-29-7 ]
  • [ 4491-33-2 ]
  • [ 25635-39-6 ]
Reference: [1] Tetrahedron, 1986, vol. 42, # 21, p. 5973 - 5977
  • 28
  • [ 4620-34-2 ]
  • [ 4491-33-2 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 35, p. 4747 - 4750
  • 29
  • [ 705966-83-2 ]
  • [ 4491-33-2 ]
  • [ 50458-79-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2004, vol. 77, # 4, p. 785 - 796
  • 30
  • [ 4491-33-2 ]
  • [ 4620-34-2 ]
Reference: [1] Patent: US2008/153871, 2008, A1, . Location in patent: Page/Page column 32
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