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Chemical Structure| 6480-68-8 Chemical Structure| 6480-68-8
Chemical Structure| 6480-68-8

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3-Quinolinecarboxylic acid is a compound with antimicrobial activity, commonly used in drug development and chemical synthesis. It exhibits biological activity by interfering with bacterial metabolic pathways.

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Product Details of 3-Quinolinecarboxylic Acid

CAS No. :6480-68-8
Formula : C10H7NO2
M.W : 173.17
SMILES Code : O=C(C1=CC2=CC=CC=C2N=C1)O
MDL No. :MFCD00006770
InChI Key :DJXNJVFEFSWHLY-UHFFFAOYSA-N
Pubchem ID :80971

Safety of 3-Quinolinecarboxylic Acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 3-Quinolinecarboxylic Acid

* 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 [ 6480-68-8 ]

[ 6480-68-8 ] Synthesis Path-Downstream   1~5

  • 2
  • [ 67-56-1 ]
  • [ 6480-68-8 ]
  • [ 53951-84-1 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride; at 0 - 80℃; The solution of quinoline-3-carboxylic acid (3 g, 17.32 mmol) in methanol (30 mL) was cooled on ice bath at 0C.Then thionyl chloride (1.264 mL, 17.32 mmol) was added and the reaction mixture was heated to 80C and maintained overnight. Reaction was monitored by TLC. After completion of reaction methanol was evaporated under reduced pressure and the resultant residue was basified with saturated sodium bicarbonate to make pH (7 to 8) to get white solid which was filtered and dried to get methyl quinoline-3- carboxylate (3.2 g, yield-99%) as a white solid; m/z-187.3.
97% With thionyl chloride; at 0℃; for 24h;Reflux; Inert atmosphere; To a precooled (0 C) solution of quinoline-3-carboxylic acid (1.50 g, 8.66 mmol) in MeOH (43 mL) under N2 atmosphere was added dropwise thionyl chloride (1.3 mL, 17 mmol). The resulting mixture was heated to reflux and stirred for 24 h, then allowed to cool to room temperature and concentrated in vacuo. The resulting residue was taken up in CH2Cl2 and quenched with sat. aq. NaHCO3. The layers were separated, and the aqueous phase was extracted with CH2Cl2 (3x). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to afford the product as an off-white solid (1.58 g, 97% yield). See, Chen, Org. Biomol. Chem.2016, 14 (24), 5505-5510. 1H NMR (500 MHz, Chloroform-d) d 9.43 (s, 1H), 8.82 (d, J = 2.0 Hz, 1H), 8.16 (d, J = 8.5 Hz, 1H), 7.94- 7.86 (m, 1H), 7.81 (ddd, J = 8.4, 6.9, 1.4 Hz, 1H), 7.60 (t, J = 7.5 Hz, 1H), 3.99 (s, 3H); 13C NMR (126 MHz, CDCl3) d 165.78, 149.83, 149.57, 139.07, 132.08, 129.33, 129.20, 127.64, 126.95, 123.12, 77.16, 52.59; IR (ATR) vmax 3509, 2994, 1714, 1618, 1572, 1497, 1434, 1367, 1290, 1241, 1192, 1100 cm-1; AMM 188.0704 (ESI) m/z [calc for C11H10NO2 (M+H)+ 188.0712].
89% With thionyl chloride; at 0℃; for 30h;Reflux; Quinoline-3-carboxylic acid (8 g, 46.2 mmol) was dissolved in methanol (900 mL), after which thionyl chloride (5 mL, 68.5 mmol)was added at 0 oC. The solution was kept at reflux, under stirring (10 h), monitoring the reaction progress by TLC (dichloromethane/methanol 9:1). An additional amount of thionyl chloride (5 mL) was added and the solution was kept at reflux (20 h). After cooling at room temperature, the solvent was evaporated at reduced pressure. To the residue water (400 mL) and 1 M sodium hydroxide (until pH 8) were added; the mixture was extracted with dichloromethane (4 x 400 mL). The collected organic phases were dried over sodium sulfate; after filtration, the solvent was removed at reduced pressure, to afford title compound 4 (7.78 g, 89%), which was used directly in the next step without any further purification. The chemical and physical properties were in agreement with the reported ones.22
89% With thionyl chloride; at 0℃; for 30h;Reflux; Quinoline-3-carboxylic acid (8 g, 46.2 mmol) was dissolved in methanol (900 mL); thionyl chloride (5 mL, 68.5 mmol) was added at 0 C. The solution was kept at reflux, under stirring (10 h), monitoring the reaction progress by TLC (dichloromethane/methanol 9:1). An additional amount of thionyl chloride (5 mL) was added and the solution was kept at reflux (20 h). After cooling at room temperature, the solvent was evaporated at reduced pressure. To the residue, water (400 ml) and 1M sodium hydroxide (until pH 8) were added; the mixture was extracted with dichloromethane (4*400 mL). The collected organic phases were dried over sodium sulfate; after filtration, the solvent was removed at reduced pressure, affording title compound 4 (7.78 g, 89%) directly used in the next step without any further purification.
75% With hydrogenchloride;Reflux; General procedure: To a suspension of the appropriate acid 17a-c (1 eq,) in MeOH (1.9 ml*mmol/eq) was added 1, 25 M HCl in MeOH solution (1.9 ml*mmol/eq). The solution was refluxed overnight, then cooled to room temperature and concentrated under vacuum. The residue was partitioned between sat. aq. NaHCO3 solution (30 ml) and EtOAc (3x35 ml). The combined organic extracts were washed with sat. aq. NaHCO3 solution (25 ml) and water (30 ml), dried over MgSO4 and concentrated under vacuum to give the pure title compounds.
74% With sulfuric acid;Reflux; Compound 3-Quinolinecarboxylic Acid (0801-131) (1.0 g, 5.78 mmol, 1.0 eq.)Dissolved in 30 ml of methanol,Then add sulfuric acid (0.5 ml),The reaction was refluxed overnight.After the reaction is completed, pH is adjusted to 8 by adding sodium bicarbonate solution.Dichloromethane extraction, liquid separation, the organic phase was dried over anhydrous sodium sulfate, spin-dry to give the product methyl 3-quinolinecarboxylate (800 mg,74%).
61% Quinoline-3-carboxylic acid (0.245 g, 1 .41 mmol) was charged in the flask with stir bar and thionyl chloride was added. The resulting mixture was allowed to stir at 80 C overnight. Upon completion, the reaction mixture was cooled to room temperature and concentrated in vacuo. MeOH was added to this crude mixture and was heated under reflux for 8 h. Upon completion, the reaction mixture was cooled to room temperature, diluted with DCM, and was washed with saturated aqueous NaHCO3. The aqueous layer was extracted with DCM twice, and the combined organic layers were dried with anhydrous Na2504. After removal of the solvents, the residue was purified by column chromatography on silica gel using EtOAc hexanes (1:6) as the eluentto give 4k (0.161 g, 61%). 1H NMR (600 MHz,CDCI3): O 9.46 (d, J= 2.1 Hz, 1H), 8.86 (d, J= 2.2 Hz, 1H), 8.17 (d, J= 8.5 Hz, 1H), 7.95 (d, J= 8.2 Hz, 1H), 7.84 (ddd, J= 8.5, 6.9, 1.4 Hz, 1H), 7.63 (ddd, J= 8.1, 6.9, 1.2 Hz, 1H), 4.03 (5, 3H). 1H NMR matches previously reported data8.
With thionyl chloride; at 0℃;Reflux; As depicted in Scheme 4-1, quinoline-3-carboxylic acid 3 was esterified with thionyl chloride in methanol to yield ester 4. Reduction of the pyridine ring of 4 with pyridine-borane complex in glacial acetic acid then delivered racemic THQ 5 whose methyl ester was saponified to yield ±-6. Alternatively, sulfonylation of ±-5 furnished compounds ±-7, which were also saponified with lithium hydroxide to afford the 3-carboxy target compounds ±-8. Further elaboration of the phenylsulfonyl group in ±-7c was accomplished by an SNAr reaction with 4- chloro-3,5-dimethylphenol followed by ester hydrolysis to afford compound ±-2, as shown in Scheme 4-2. In addition, the phenylsulfonyl moiety in ±-2 was replaced with a more flexible propylene group through a reductive amination-saponification sequence to yield ±-11.

  • 3
  • [ 6480-68-8 ]
  • [ 53951-84-1 ]
YieldReaction ConditionsOperation in experiment
65% In tetrahydrofuran; methanol; hexane; Step 1: Quinoline-3-carboxylic acid methyl ester. To a stirred solution, of quinoline-3-carboxylic acid (346 mg, 2 mmol) dissolved in 4:1 THF:MeOH (6 mL) at 0 C. was added TMS-diazomethane (2in hexane) portionwise until a diazomethane yellow color persisted. The reaction was concentrated to the give the methyl ester as a tan solid (244 mg, 65%). 1H-NMR (400 MHz, CDCl3) delta9.44 (s, 1H), 8.85 (s, 1 H), 8.17 (d, 1H), 7.96 (d, 11H), 7.84 (dd, 1H), 7.62 (dd, 11H), 4.02 (s, 3H)
With thionyl chloride; In methanol; at 0 - 80℃; for 14h; Compound 16-a (1.00 g, 5.77 mmol, 1.00 eq) was dissolved in methanol (15.00 mL), and thionyl chloride (2.06 g, 17.31 mmol, 1.26 mL, 3.00 eq) was added thereto at 0C. The above reaction solution was stirred at 80C for 14 hours. After the reaction was completed, the reaction solution was spin-dried, to give the product of compound 16-b (1.00 g, crude), which was used directly in the next step without purification. 1H NMR (400 MHz, methanol) delta =9.82 (s, 1H), 9.72 (s, 1H), 8.52-8.58 (m, 1H), 8.30-8.42 (m, 2H), 8.05-8.14 (m, 1H), 4.13 (s, 3H).
  • 4
  • [ 6480-68-8 ]
  • [ 3171-46-8 ]
  • [ 1339147-86-2 ]
  • 5
  • [ 6480-68-8 ]
  • [ 36887-98-6 ]
  • C19H17N3O [ No CAS ]
 

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