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[ CAS No. 5466-31-9 ]

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Chemical Structure| 5466-31-9
Chemical Structure| 5466-31-9
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Product Details of [ 5466-31-9 ]

CAS No. :5466-31-9 MDL No. :MFCD00085413
Formula : C16H10ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :283.71 g/mol Pubchem ID :-
Synonyms :

Safety of [ 5466-31-9 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P270-P273-P301+P312-P330-P501 UN#:
Hazard Statements:H302-H413 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5466-31-9 ]

  • Downstream synthetic route of [ 5466-31-9 ]

[ 5466-31-9 ] Synthesis Path-Downstream   1~16

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YieldReaction ConditionsOperation in experiment
85% With potassium hydroxide; In ethanol;Reflux; General procedure: A mixture of isatin or 5-methoxyisatin (10 mmol), 33% potassiumhydroxide (10 mL) in ethanol (20 mL), and appropriate acetophenone derivative (10 mmol) was heated under reflux for 9e18 h. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water (50 mL) and extracted with ether (3 50 mL). The aqueous layer was neutralized with 1 M hydrochloric acid. The formed precipitate was filtered off, washed with water, dried, and crystallized from ethanol.
80% With potassium hydroxide; In ethanol;Reflux; satin (4a) or 5-methoxyisatin (4b) (10 mmol), 33% potassium hydroxide (10 mL), ethanol (20 mL), and appropriate acetophenone derivative (10 mmol) was mixed and heated under reux for 18-24 hr. The reaction mixture was concentrated under reduced pressure; the residue was diluted with water (50 mL) and extracted with diethylether (3 x 50 mL). The aqueous layer was neutralized with 1 M hydrochloric acid. The precipitated solid was ltered, washed with water, dried and crystallized from ethanol
51% In ethanol; General Method A 2-(4-chlorophenyl)quinoline-4-carboxylic acid (Intermediate 1) To a stirred solution of isatin (30.0 g, 204 mmol) in 500 mL ethanol, 4-chloroacetophenone (47.0 g, 244 mol) was added in one portion. Potassium hydroxide flakes (22.8 g, 408 mmol) were added in several portions and the reaction was heated to reflux for 14 hr. The reaction was diluted with 1 liter water and washed with ethyl acetate (3*300 mL). The aqueous layer was cooled in an ice-bath and acidified with glacial acetic acid. The precipitated product was filtered, washed with cold, dilute acetic acid and dried in vacuum to give analytically pure intermediate 1 (29.5 g, 51%). TLC: 30% EtOAc/Hexanes (Rf: 0.2) 1H NMR (400 MHz, DMSO-d6) δ8.59 (d, J=8.6 Hz, 1H), 8.37 (s, 1H), 8.23 (d, J=8.5 Hz, 2H), 8.11 (d, J=8.5 Hz, 1H), 7.82 (t, J=7.7 Hz, 1H), 7.68 (t, J=7.7 Hz, 1H), 7.57 (d, J=8.3 Hz, 2H). LC-MS (ESI+): m/z 284.5 [M+H]+.
Ca.100% With potassium hydroxide; In water; for 16h;Reflux; Inert atmosphere; Isatin (1 g, 6.8 mmol, 1 equiv) was dissolved 33% w/v aqueous KOH solution. Acetophenone (6.8 mmol, 1 equiv) was added and the reaction mixture was gently heated to reflux. The reaction was refluxed for 16 h. After the reaction time, the mixture was cooled to rt then transferred to an Erlenmeyer flask and subsequently cooled to 0 C. Carefully, the reaction mixture was acidified with dropwise addition of cone. HCI and provided the carboxylic acid product as a yellow solid after collection by vacuum filtration. The carboxylic acid (1 g, 1 equiv) was dissolved in 50 ml of diethyl ether and cooled to 0 C. Lithium aluminum hydride (1.2 equiv) was added portion-wise at 0 C and the reaction mixture was allowed to warm to rt, while stirring, overnight. The Feiser work-up was used to isolate the reduced product after removal of the organic solvent by reduced pressure. The alcohol was used without further purification. The alcohol (1 equiv) was dissolved in 10 ml dimethyl sulfoxide (dried over molecular sieves). IBX (2 equiv) was added to the reaction mixture at rt and the reaction was allowed to stir overnight at rt. The reaction mixture was quenched with diH20. The aqueous layer was extracted three times with ethyl acetate and the combined organic layer was washed with 1 M NaOH, water and brine. The organic layer was then dried with sodium sulfate and the solvent was removed by reduced pressure. [00332] 2-(4-Chlorophenyl)-4-quinolinecarboxylic acid: [00333] A yellow solid was obtained in near quantitative yield (1 .9 g). Spectral data correspond to that reported.23 1H NMR (400 MHz, DMSO-cfe): δ 9.03 (dd, J = 8.2, 1.5 Hz, 1 H), 8.43 - 8.38 (app d of AA'BB', 2 H), 8.21 (dd, J = 8.8, 0.9 Hz, 1 H), 7.88 (ddd, J = 8.4, 6.9, 1.4 Hz, 1 H), 7.75 (ddd, J = 8.3, 6.9, 1.3 Hz, 1 H), 7.63 - 7.58 (app d of AA'BB', 2 H).
With potassium hydroxide; In ethanol;Reflux; General procedure: 10 mmol Isatin (1) was added into a stirred solutionof 33% potassium hydroxide (10 mL) and ethanol(20 mL). 10 mmol of appropriate acetophenone derivative(IIa-j) was mixed and heated under reflux for18-24 h. The reaction mixture was poured on crushedice and the pH was adjusted by the solution of 2 N HClto 6-7. The precipitated solid was filtered, washedwith water, dried and crystallized from ethanol whichwas then taken to the next step without any furtherpurification [29, 30].
General procedure: To a solution of 33% KOH (aqueous, 6.8 mL) in MeOH (15 mL), isatin(A1, 1.00 g, 6.8 mmol) was reacted with 4′-methylacetophenone (B1,0.91 g, 6.8 mmol) at 100 for 24 h. After reaction, the solvent wasevaporated in vacuum, and the residue dissolved in water. Hydrochloricacid was used to adjust the pH to 2, and white solid was precipitated.Suction filtration was used to collect the white solid, which was thenvacuum dried to produce the intermediate C1 (1.20 g, yield 67%).

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  • N-[α-(methoxycarbonyl)benzyl]-2-(4-chlorophenyl)quinoline-4-carboxamide [ No CAS ]
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  • [2-(4-Chloro-phenyl)-quinoline-4-carbothioyl]-methyl-amino}-acetic acid [ No CAS ]
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  • 2-chloro-1-[2-(4-chloro-phenyl)-[4]quinolyl]-ethanone [ No CAS ]
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  • [ 408326-15-8 ]
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  • 2-bromo-1-[2-(4-chloro-phenyl)-[4]quinolyl]-ethanol [ No CAS ]
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  • [ 412041-86-2 ]
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  • 2,2-dibromo-1-[2-(4-chloro-phenyl)-[4]quinolyl]-ethanone [ No CAS ]
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  • H2O [ No CAS ]
  • NaHCO3 [ No CAS ]
  • [ 5466-31-9 ]
  • [ 543-27-1 ]
  • N-[α-(methoxycarbonyl)benzyl]-2-(4-chlorophenyl)quinoline-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In Et2O; EXAMPLE 93 (R,S)-N-(α-(Methoxycarbonyl)benzyl]-2-(p-chlorophenyl)quinoline-4-carboxamide 2 g (7.0 mmol) of 2-(p-chlorophenyl)quinoline-4-carboxylic acid and 1.7 ml (15.4 mmol) of N-methylmorpholine were dissolved, under nitrogen athmosphere, in 50 ml of dry THF.. The solution was cooled to -20C and 0.91 ml (7.0 mmol) of isobutyl chloroformate were added.. After 20 minutes, 2.12 g (10.5 mmol) of methyl (R,S) phenylglycinate hydrochloride and 1.3 ml (11.9 mmol) of N-methylmorpholine, dissolved in 30 ml of dry THF, were added and the reation mixture was stirred at room temperature overnight.. 5 ml of H2O were added and the reaction mixture was evaporated in vacuoto dryness.. The residue was dissolved in Et2O, washed with a saturated solution of NaHCO3, separated, dried over Na2SO4and evaporated in vacuoto dryness.. The residual oil was flash chromatographed on 230-400 mesh silica gel, eluding with a mixture of hexane/isopropyl ether 7: 3 to afford 0.9 g of crude product, which was recrystallized three times with IPrO2/toluene to yield 0.5 g of the title compound. . C25H19ClN2O3 M.P. = 170-172 C
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  • methyl (R,S) phenylglycinate hydrochloride [ No CAS ]
  • [ 5466-31-9 ]
  • [ 543-27-1 ]
  • N-[α-(methoxycarbonyl)benzyl]-2-(4-chlorophenyl)quinoline-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; water; EXAMPLE 93 (R,S)-N-[α-(Methoxycarbonyl)benzyl]-2-(p-chlorophenyl)quinoline-4-carboxamide 2 g (7.0 mmol) of 2-(p-chlorophenyl)quinoline-4-carboxylic acid and 1.7 ml (15.4 mmol) of N-methylmorpholine were dissolved, under nitrogen athmosphere, in 50 ml of dry THF. The solution was cooled to -20 C. and 0.91 ml (7.0 mmol) of isobutyl chloroformate were added. After 20 minutes, 2.12 g (10.5 mmol) of methyl (R,S) phenylglycinate hydrochloride and 1.3 ml (11.9 mmol) of N-methylmorpholine, dissolved in 30 ml of dry THF, were added and the reaction mixture was stirred at room temperature overnight. 5 ml of H2O were added and the reaction mixture was evaporated in vacuo to dryness. The residue was dissolved in Et2O, washed with a saturated solution of NaHCO3, separated, dried over Na2SO4 and evaporated in vacuo to dryness. The residual oil was flash chromatographed on 230-400 mesh silica gel, eluding with a mixture of hexane/isopropyl ether 7:3 to afford 0.9 g of crude product, which was recrystallized three times with iPrO2/toluene to yield 0.5 g of the title compound.
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