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[ CAS No. 23789-85-7 ] {[proInfo.proName]}

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Chemical Structure| 23789-85-7
Chemical Structure| 23789-85-7
Structure of 23789-85-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 23789-85-7 ]

CAS No. :23789-85-7 MDL No. :MFCD00973691
Formula : C13H13NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 231.25 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 23789-85-7 ]

* 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.

  • Downstream synthetic route of [ 23789-85-7 ]

[ 23789-85-7 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 64-17-5 ]
  • [ 18471-99-3 ]
  • [ 23789-85-7 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride
  • 2
  • [ 52980-28-6 ]
  • [ 74-88-4 ]
  • [ 23789-85-7 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 60℃; for 8h;
78% Stage #1: ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate With sodium hydride In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 60℃; for 4h; Inert atmosphere;
70% Stage #1: ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 60℃; for 1h; 7.1.3. Synthesis of ethyl-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (6) Ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (5)(1.15 mmol) and DMF (5 mL) were placed in a round bottom flask.Then, K2CO3 (1.72 mmol)was added, and the reactionwas stirred atroom temperature in argon atmosphere. At that time, CH3I(2.30 mmol) was introduced dropwise. The reaction was stirred at60 C for 1 h. After, the mixture was diluted with water andextracted with DCM (3 15 mL). The combined organic layers weredried over anhydrous Na2SO4, and the solvent was evaporatedunder reduced pressure. The crude product was crystallised fromDCM (70% yield). 1H NMR (400 MHz, CDCl3) d: 8.53 (1H, dd, J 8.0,1.6, 0.6 Hz, H5), 8.46 (1H, s, H2), 7.70 (1H, dd, J 8.6, 7.2,1.6 Hz, H7),7.49e7.39 (2H, m, H8, H6) 4.40 (2H, q, J 7.1 Hz, CH2), 3.88 (3H, s,NCH3), 1.42 (3H, t, J 7.1 Hz, CH3).
With thallium (I) ethoxide 1.) ethanol, Rt, 2 h; 2.) without solvent, 70 - 80 deg C, 4 h; Yield given. Multistep reaction;

  • 3
  • [ 23789-85-7 ]
  • [ 18471-99-3 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydroxide In water for 4h; Reflux; 7.1.4. Synthesis of 1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) A suspension of ethyl-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (6) (4.41 mmol) in 10% aq. NaOH (12 mL) wasrefluxed for 4 h. After cooling to room temperature, the mixturewas acidified with conc. HCl until pH 3. The resulting solid wasfiltered and washed with water (95% yield). 1H NMR (400 MHz,DMSO-d6) d: 15.26 (1H, s, COOH), 9.06 (1H, s, H2), 8.39 (1H, dd,J 8.1, 1.5, 0.7 Hz, H5), 8.04e7.94 (2H, m, H7, H8), 7.70 (1H, dd,J 8.1, 6.2, 1.8 Hz, H6), 4.11 (3H, s, NCH3).
94% With potassium hydroxide In water at 100℃; for 3h;
With sodium hydroxide for 1h; Heating;
  • 4
  • [ 26892-90-0 ]
  • [ 74-88-4 ]
  • [ 23789-85-7 ]
  • 5
  • [ 54535-22-7 ]
  • [ 23789-85-7 ]
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