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[ CAS No. 6925-00-4 ]

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Chemical Structure| 6925-00-4
Chemical Structure| 6925-00-4
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CAS No. :6925-00-4 MDL No. :MFCD01365834
Formula : C9H6N2O2 Boiling Point : 355.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :174.16 g/mol Pubchem ID :674813
Synonyms :

Safety of [ 6925-00-4 ]

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

Application In Synthesis of [ 6925-00-4 ]

  • Upstream synthesis route of [ 6925-00-4 ]
  • Downstream synthetic route of [ 6925-00-4 ]

[ 6925-00-4 ] Synthesis Path-Upstream   1~10

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Reference: [1] Patent: WO2016/77232, 2016, A2,
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YieldReaction ConditionsOperation in experiment
89% With acetic acid In ethanol at 75℃; Stage 1 Compound (iii) is heated in ethanol and acetic acid with glyoxal at 75° C. The resulting suspension is cooled to 5° C. and filtered. The resulting Compound (iv) wetcake is washed with cold ethanol and dried under vacuum at 50° C.
71% at 20℃; Quinoline-6-carboxylic Acid (Intermediate Compound)To a mixture of 3,4-diaminobenzoic acid (30.0 g; 197 mmol) and ethanol (300 ml; 99percent), was added: a mixture of 40percent aqueous glyoxal (33 ml; 227 mmol) in ethanol (75 ml, 99percent) was added at room temperature. The mixture was allowed to stir overnight at room temperature. The product was isolated as a grey powder by filtration. Yield 24.4 g (71percent).
Reference: [1] Patent: US2007/179144, 2007, A1, . Location in patent: Page/Page column 5; 6
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 4, p. 815 - 820
[3] Patent: US2009/286797, 2009, A1, . Location in patent: Page/Page column 6
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3771 - 3774
[5] European Journal of Medicinal Chemistry, 2012, vol. 48, p. 255 - 264
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YieldReaction ConditionsOperation in experiment
76.6%
Stage #1: With sodium hydroxide In ethanol; water for 4 h; Heating / reflux
Stage #2: With hydrogenchloride In ethanol; water
Preparation Example I-1.
Quinoxaline-6-carboxylic acid
To a solution of quinoxaline-6-carboxylic acid methyl ester (2084mg, 11.07mmol) in ethanol (25mL) was added an aqueous solution of 1 N sodium hydroxide (25mL), and the solution was stirred for 4 hours under reflux.
1 N Hydrochloric acid was added to the reaction mixture to adjust the pH to 4, then, the precipitated solid was collected by filtration, washed with water and isopropanol, then dried to obtain the title compound (1477mg, 8.479mmol, 76.6percent) as a solid.
1H-NMR Spectrum (DMSO-d6) δ (ppm): 8.18 (1 H, d, J=8.4Hz), 8.29 (1H, dd, J=8.4, 1.2Hz), 8.61 (1 H, d, J=1.2Hz), 9.00-9.07 (2H, m).
76.6%
Stage #1: for 4 h; Heating / reflux
Stage #2: With hydrogenchloride In water
To a solution of quinoxaline-6-carboxylic acid methyl ester (2084mg, 11.07mmol) in ethanol (25mL) was added an aqueous solution of 1 N sodium hydroxide (25mL), and the solution was stirred for 4 hours under reflux. 1 N Hydrochloric acid was added to the reaction mixture to adjust the pH to 4, then, the precipitated solid was collected by filtration, washed with water and isopropanol, then dried to obtain the title compound (1477mg, 8.479mmol, 76.6percent) as a solid. 1H-NMR Spectrum (DMSO-d6) δ(ppm) : 8.18 (1H, d, J=8.4Hz), 8.29 (1H, dd, J=8.4, 1.2Hz), 8.61 (1 H, d, J=1.2Hz), 9.00-9.07 (2H, m).
Reference: [1] Patent: EP1782811, 2007, A1, . Location in patent: Page/Page column 59
[2] Patent: EP1669348, 2006, A1, . Location in patent: Page/Page column 67
[3] Patent: WO2006/14618, 2006, A2, . Location in patent: Page/Page column 40
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YieldReaction ConditionsOperation in experiment
61% at 120℃; for 23 h; Inert atmosphere; Molecular sieve General procedure: A mixture of phenylenediamine (0.9 mmol), diol or aminoalcohol (4.5 mmol), CsOH.H2O (1.8 mmol), complex 3b and molecular sieves (0.3 g) in a reaction tube was flushed with oxygen gas. The reaction mixture was heated in a oil bath at 120 C for 23 h. After cooling, water and ethyl acetate were added. The organic extracts were separated, dried and concentrated. The desired product was purified by chromatography with CH2Cl2/EtOAc 10/1as eluent.
Reference: [1] Journal of Organometallic Chemistry, 2014, vol. 775, p. 94 - 100
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Reference: [1] Patent: US6432949, 2002, B1,
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Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 1, p. 71 - 85
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Reference: [1] Chemische Berichte, 1953, vol. 86, p. 1295,1301
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Reference: [1] Chemische Berichte, 1953, vol. 86, p. 1295,1301
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3771 - 3774
[2] European Journal of Medicinal Chemistry, 2012, vol. 48, p. 255 - 264
[3] Patent: WO2013/40515, 2013, A1,
[4] Patent: WO2013/43935, 2013, A1,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3771 - 3774
[2] European Journal of Medicinal Chemistry, 2012, vol. 48, p. 255 - 264
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