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Chemical Structure| 81918-01-6 Chemical Structure| 81918-01-6

Structure of 81918-01-6

Chemical Structure| 81918-01-6

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Product Details of [ 81918-01-6 ]

CAS No. :81918-01-6
Formula : C14H16ClNO5
M.W : 313.73
SMILES Code : O=C(OCC)C(NC(C1=CC=C(Cl)C=C1)=O)C(OCC)=O
MDL No. :MFCD09031363

Safety of [ 81918-01-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 81918-01-6 ]

* 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 [ 81918-01-6 ]

[ 81918-01-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 64-17-5 ]
  • [ 4876-10-2 ]
  • [ 81918-01-6 ]
  • [ 90098-04-7 ]
YieldReaction ConditionsOperation in experiment
7.18 g (92.17%) With hydrogenchloride; sodium hydroxide; sodium ethanolate; In water; EXAMPLE 9 Synthesis of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic Acid 100 ml of anhydrous ethyl alcohol and 2.23 g of sodium ethoxide (96percent) were added to a 500 ml flask, and the mixture was cooled down to below 5° C. After adding 7.91 g of diethyl 4-chlorobenzamidomalonate, the resulting solution was stirred at below 5° C. for one hour. 5.00 g of 4-bromomethylquinolinon was added to the mixture and the resulting solution was stirred at the room temperature for 16 hours to produce an intermediate, ethyl 2-(4-chlorobenzoylamino)-2-ethoxycarbonyl-3-[2(1H)-quinolinon-4-yl]propionate. After the completion of the reaction, 2.71 g of sodium hydroxide (93percent) was dissolved in 30 ml of purified water and this aqueous solution was added to the above solution, which was then stirred at the room temperature for about 2 hours. Subsequently, the resulting solution was warmed to about 60° C. and stirred for 2 hours to complete the reaction. The ethyl alcohol was removed through vacuum concentration, and purified water and 1N HCl were added to the residue for crystallization. The crystal thus obtained was filtered and then subjected to recrystallization with DMF and water to yield 7.18 g (92.17percent) of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid. The data of melting point and 1H NMR were the same as those in Example 4.
7.17 g (92.04%) With hydrogenchloride; potassium hydroxide; sodium ethanolate; EXAMPLE 13 Synthesis of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic Acid 100 ml of anhydrous ethyl alcohol and 2.23 g of sodium ethoxide (96percent) were added to a 500 ml flask, and the mixture was cooled down to below 5° C. After adding 7.91 g of diethyl 4-chlorobenzamidomalonate, the resulting solution was stirred at below 5° C. for one hour. 5.00 g of 4-bromomethylquinolinon was added to the mixture and the resulting solution was stirred at the room temperature for 16 hours to produce an intermediate, ethyl 2-(4-chlorobenzoylamino)-2-ethoxycarbonyl-3-[2(1H)-quinolinon-4-yl]propionate. After the completion of the reaction, 3.93 g of potassium hydroxide (90percent) was added to the above solution, which was then stirred at the room temperature for about 2 hours. Subsequently, the resulting solution was warmed to about 60° C. and stirred for 4 hours to complete the reaction. The concentrated hydrochloric acid were added to the residue for crystallization. The crystal thus obtained was filtered and then subjected to recrystallization with DMF and water to yield 7.17 g (92.04percent) of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid. The data of melting point and 1H NMR were the same as those in Example 4.
7.08 g (90.88%) With hydrogenchloride; potassium hydroxide; sodium ethanolate; In water; EXAMPLE 11 Synthesis of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic Acid 100 ml of anhydrous ethyl alcohol and 2.23 g of sodium ethoxide (96percent) were added to a 500 ml flask, and the mixture was cooled down to below 5° C. After adding 7.91 g of diethyl 4-chlorobenzamidomalonate, the resulting solution was stirred at below 5° C. for one hour. 5.00 g of 4-bromomethylquinolinon was added to the mixture and the resulting solution was stirred at the room temperature for 16 hours to produce an intermediate, -ethyl 2-(4-chlorobenzoylamino)-2-ethoxycarbonyl-3-[2(1H)-quinolinon-4-yl]propionate. After the completion of the reaction, 3.93 g of potassium hydroxide (90percent) was dissolved in 30 ml of purified water and this aqueous solution was added to the above solution, which was then stirred at the room temperature for about 2 hours. Subsequently, the resulting solution was warmed to about 60° C. and stirred for 2 hours to complete the reaction. The ethyl alcohol was removed through vacuum concentration, and purified water and 1N HCl were added to the residue for crystallization. The crystal thus obtained was filtered and then subjected to recrystallization with DMF and water to yield 7.08 g (90.88percent) of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid. The data of melting point and 1H NMR were the same as those in Example 4.
7.15 g (91.78%) With hydrogenchloride; sodium hydroxide; sodium ethanolate; EXAMPLE 12 Synthesis of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic Acid 100 ml of anhydrous ethyl alcohol and 2.23 g of sodium ethoxide (96percent) were added to a 500 ml flask, and the mixture was cooled down to below 5° C. After adding 7.91 g of diethyl 4-chlorobenzamidomalonate, the resulting solution was stirred at below 5° C. for one hour. 5.00 g of 4-bromomethylquinolinon was added to the mixture and the resulting solution was stirred at the room temperature for 16 hours to produce an intermediate, ethyl 2-(4-chlorobenzoylamino)-2-ethoxycarbonyl-3-[2(1H)-quinolinon-4-yl]propionate. After the completion of the reaction, 2.71 g of sodium hydroxide (93percent) was added to the above solution, which was then stirred at the room temperature for about 2 hours. Subsequently, the resulting solution was warmed to about 60° C. and stirred for 4 hours to complete the reaction. The concentrated hydrochloric acid were added to the residue for crystallization. The crystal thus obtained was filtered and then subjected to recrystallization with DMF and water to yield 7.15 g (91.78percent) of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid. The data of melting point and 1H NMR were the same as those in Example 4.
6.7 g (86.0%) With hydrogenchloride; sodium hydroxide; sodium ethanolate; In water; EXAMPLE 10 Synthesis of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic Acid 100 ml of anhydrous ethyl alcohol and 2.23 g of sodium ethoxide (96percent) were added to a 500 ml flask, and the mixture was cooled down to below 5° C. After adding 7.91 g of diethyl 4-chlorobenzamidomalonate, the resulting solution was stirred at below 5° C. for one hour. 5.00 g of 4-bromomethylquinolinon was added to the mixture and the resulting solution was stirred at the room temperature for 16 hours to produce an intermediate, ethyl 2-(4-chlorobenzoylamino)-2-ethoxycarbonyl-3-[2(1H)-quinolinon-4-yl]propionate. After the completion of the reaction, 2.71 g of sodium hydroxide (93percent) was dissolved in 30 ml of purified water and this aqueous solution was added to the above solution, which was then stirred at the room temperature for about 2 hours. Subsequently, the resulting solution was warmed to about 60° C. and stirred for 2 hours to complete the reaction. The ethyl alcohol was removed through vacuum concentration, and purified water and 1N HCl were added to the residue for crystallization. The crystal thus obtained was filtered and then subjected to recrystallization with methanol and potassium hydroxide to yield 6.7 g (86.0percent) of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid. The data of melting point and 1H NMR were the same as those in Example 4.

  • 2
  • [ 64-17-5 ]
  • [ 4876-10-2 ]
  • [ 81918-01-6 ]
  • [ 1028268-32-7 ]
YieldReaction ConditionsOperation in experiment
8.02 g (81.1%) With sodium; In water; EXAMPLE 3 Synthesis of Ethyl 2-(4-chlorobenzoylamino)-2-ethoxycarbonyl-3-[2(1H)-quinolinon-4-yl]propionate Sodium ethylate was prepared from 0.48 g of sodium and 100 ml of anhydrous ethyl alcohol. After adding 6.59 g of diethyl 4-chlorobenzamidomalonate, the mixture was stirred at the room temperature for one hour. 5.00 g of 4-bromomethylcarbostyril was added and the mixture was subjected to reflux stirring for 2 hours. After the completion of the reaction, the ethyl alcohol was removed through vacuum distillation and water was added to the residue for crystallization. The crystal thus obtained was filtered and dried to yield 8.02 g (81.1%) of ethyl 2-(4-chlorobenzoylamino)-2-ethoxycarbonyl-3-[2(1H)-quinolinon-4-yl]propionate. Melting point: 213.3~214.5 C.; and 1H NMR (CDCl3, 500 MHz) (ppm): 1.29-1.32 (m,6H), 4.05 (s,2H), 4.24-4.36 (m,4H), 6.45 (s,1H), 6.98-7.00 (m,1H), 7.33-7.41 (m,4H), 7.54-7.56 (m,1H), 7.70-7.71 (d,2H), 12.19 (br,1H).
  • 3
  • [ 4876-10-2 ]
  • [ 81918-01-6 ]
  • [ 1028268-32-7 ]
YieldReaction ConditionsOperation in experiment
88% 2) 0.96g of sodium was added to 200ml of absolute ethanol,Heat until the sodium is completely dissolved in ethanol,Cooled to room temperature for use; then 13.2g of the product obtained in step 1)Diethyl 4-chlorobenzamidomalonate was added to sodium ethoxide solution,Stir at room temperature for 1.5h, and then add 9.8g dropwise to the reaction mixture 4 - bromomethyl quinolone, stirred at room temperature to the point of disappearance of raw materials,After the reaction was completed, the ethanol was concentrated under reduced pressure to obtain a crude product2- (4-chlorobenzamido) -2-Ethoxycarbonyl-3-[2 (1H) -quinuclidin-4-yl]Ethyl propionate,The crude product was placed in a mixed solvent of dichloromethane and water recrystallization,Get fine2- (4-chlorobenzamido) -2-Ethoxycarbonyl-3- [2 (1H) -4-yl] propionate17.6g (yield: 88%).
 

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