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[ CAS No. 52980-28-6 ]

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CAS No. :52980-28-6 MDL No. :MFCD01314279
Formula : C12H11NO3 Boiling Point : 343.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :217.22 g/mol Pubchem ID :220876
Synonyms :

Safety of [ 52980-28-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
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Application In Synthesis of [ 52980-28-6 ]

  • Upstream synthesis route of [ 52980-28-6 ]
  • Downstream synthetic route of [ 52980-28-6 ]

[ 52980-28-6 ] Synthesis Path-Upstream   1~3

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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6505 - 6510
[2] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 23, p. 2661 - 2664
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1448 - 1452
[4] ChemBioChem, 2014, vol. 15, # 9, p. 1280 - 1285
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 2, p. 384 - 388
[6] Journal of Enzyme Inhibition and Medicinal Chemistry, 2018, vol. 33, # 1, p. 171 - 183
[7] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 12, p. 1205 - 1210
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YieldReaction ConditionsOperation in experiment
80% at 0 - 80℃; for 16 h; Ex mple 2: Synthesis of 4-Oxo-l,4-dihydroquinoline-3-carboxylic acid (3): (0084) (0085) To a suspension of ethyl 4-oxo- l,4-dihydroquinoline-3-carboxylate (2) (0.5 g, 2.30 mmol) in THF (10 mL), a solution of aqueous 1 M LiOH (aq) (4.60 mL, 4.60 mmol) was added drop wise at 0 °C, and then the reaction mixture was heated at 80 °C for 16h. Reaction mass was evaporated to dryness, dissolved in H20 (5 mL), washed with diethyl ether (2x5 mL).The aqueous layer was acidified with 1 M HC1 (aq),compound thus precipitated was filtered, dried under vacuum to give desired compound as off-white solid. Yield: (0.35g; 80percent) 1H NMR (400MHz ,DMSO-d6) δ = 15.36 (brs, 1H), 13.43 (brs, 1H), 8.91 (s, 1H), 8.31 (d, J = 8.3 Hz, 1H), 7.98 - 7.75 (m, 2H), 7.62 (t, J = 7.6 Hz, 1H).
75% With sodium hydroxide In ethanol for 5 h; Reflux General procedure: A suspension of ester 3e–k (2 mmol) in 4percent NaOHhydroalcoholic solution (5 ml) was refluxed until no startingmaterial could be detected by Thin Layer Chromatography(5 h). After cooling, the mixture was completely acidifiedby adding concentrated HCl and the solid obtained wascollected by filtration, washed with water, and crystallizedfrom ethanol to afford compound 4e–k. 4-Oxo-1,4-dihydroquinoline-3-carboxylic acid (4e) Starting from 3e (1 g); Yield (white powder): 600 mg(75 percent); m.p. 280 °C (decomposed); IR (KBr) νmax1400–1600 (aromatic), 1717 (carbonyl), 2790–3260 (acidicOH) cm−1; 1H-NMR (DMSO-d6, 500 MHz) δ = 7.59–7.63 (1H, t, J = 7.2 Hz, H6), 7.83 (1H, d, J = 8.2 Hz, H8), 7.90(1H, t, J = 7.0 Hz, H7), 8.30 (1H, d, J = 7.3 Hz, H5), 8.90(1H, s, H2), 13.42 (1H, br s, enolic OH), 15.34 (1H, br s,carboxylic OH); 13C-NMR (DMSO-d6, 60 MHz) δ = 105.3(C, C-3), 119.7 (CH, C-9), 123.6 (CH, C-7), 125.6 (CH,C-6), 125.9 (C, C-5), 133.9 (CH, C-8), 138.5 (C,C-10), 158.9 (CH, C-2), 167.2 (C,COOH), 178.5 (C, C=O);LC-MS (ESI) m/z 212.1 (M+Na+); Anal. Calcd. forC10H7NO3: C, 63.49; H, 3.73; N, 7.40. Found: 63.62; H,3.96; N, 7.69.
7.5 g at 80 - 85℃; for 3 h; In a clean round bottom flask, ethyl 4-oxo-l, 4-dihydroquinoline-3-carboxylate (10.0 gm) was charged to a solution of sodium hydroxide (3.7 gm) in 13.0 ml water. The reaction mass was heated for 3.0 hr at 80-85 C and then cooled to 25-30. To this was added 0.10 gm of activated charcoal and filtered. The pH was adjusted using con HCL and the product was filtered and washed with water. The wet cake slurried in methanol at 25 -30 C and filtered. The product was dried under vacuum at 50.0 C to get 7.50 gm of title productPurity by HPLC - 99.75 percent
Reference: [1] Chemical Communications, 2005, # 43, p. 5438 - 5440
[2] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 6, p. 3169 - 3173
[3] Patent: WO2017/208253, 2017, A2, . Location in patent: Page/Page column 13-14
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5405 - 5418
[5] Medicinal Chemistry Research, 2016, vol. 25, # 9, p. 1861 - 1876
[6] Journal of Medicinal Chemistry, 2006, vol. 49, # 22, p. 6443 - 6450
[7] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 17, p. 5261 - 5265
[8] Patent: WO2010/108155, 2010, A1, . Location in patent: Page/Page column 14; 33-34
[9] Patent: WO2010/108162, 2010, A1, . Location in patent: Page/Page column 62-64
[10] Patent: US2011/230519, 2011, A1, . Location in patent: Page/Page column 15-16
[11] Patent: WO2013/67410, 2013, A1, . Location in patent: Paragraph 0083
[12] Patent: WO2013/185112, 2013, A1, . Location in patent: Paragraph 00536
[13] Patent: WO2014/71122, 2014, A1, . Location in patent: Paragraph 00156; 00321; 00322; 00325; 00327
[14] Patent: WO2014/118805, 2014, A1, . Location in patent: Paragraph 0290
[15] Patent: US2014/221424, 2014, A1, . Location in patent: Paragraph 0077
[16] Patent: WO2015/73231, 2015, A1, . Location in patent: Paragraph 00340-00341
[17] Patent: WO2015/189560, 2015, A1,
[18] Patent: US2017/96397, 2017, A1, . Location in patent: Paragraph 0093
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Reference: [1] ACS Medicinal Chemistry Letters, 2018,
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