4-chloro-benzoyl chloride
rebamipide
Conditions | Yield |
---|---|
Stage #1: 2-amino-3-[2(1H)-quinolinone-4-yl]propionic acid dihydrochloride dihydrate; 4-chloro-benzoyl chloride With sodium hydroxide In water; acetone at 0℃; Stage #2: With hydrogenchloride In water; acetone | 96.9% |
2-amino-3-[6-bromo-2(1H)-quinolon-4-yl]propionic acid
4-chloro-benzoyl chloride
2-amino-3-<2-(1H)-quinolinon-4-yl>propionic acid hydrochloride
rebamipide
Conditions | Yield |
---|---|
Stage #1: 2-amino-3-[6-bromo-2(1H)-quinolon-4-yl]propionic acid; 2-amino-3-<2-(1H)-quinolinon-4-yl>propionic acid hydrochloride With sodium hydroxide; hydrogen; Raney nikel In water at 20℃; for 2h; Stage #2: 4-chloro-benzoyl chloride With sodium hydroxide In water; acetone at 0℃; Stage #3: With hydrogenchloride In water; acetone | 96.2% |
ethyl 2-(4-chlorobenzamido)-2-ethoxyoxo-3-[2-(1H)-quinolin-4-yl]propionate
rebamipide
Conditions | Yield |
---|---|
With water; sodium hydroxide In ethanol Reflux; | 94% |
rebamipide
Conditions | Yield |
---|---|
With ethanol; sodium hydroxide at 60 - 65℃; for 3h; | 93% |
2(1H)-quinolinon-4-ylpropionic acid
4-chloro-benzoyl chloride
rebamipide
Conditions | Yield |
---|---|
With Lindlar's catalyst; ammonia In toluene at 90℃; under 375.038 Torr; for 2h; Reagent/catalyst; Inert atmosphere; Autoclave; Green chemistry; | 89% |
4-chloro-benzoyl chloride
2‐amino‐3‐[2(1H)‐quinolinon‐4‐yl]propionic acid
rebamipide
Conditions | Yield |
---|---|
With sodium hydroxide In water at 0 - 20℃; for 18h; Inert atmosphere; | 59% |
With potassium hydroxide In tetrahydrofuran; water at 0 - 15℃; for 2.5h; Reagent/catalyst; Solvent; Temperature; |
4-chloro-benzoyl chloride
2-amino-3-<2-(1H)-quinolinon-4-yl>propionic acid hydrochloride
rebamipide
Conditions | Yield |
---|---|
With potassium carbonate In water; acetone for 2h; | 49% |
4-bromomethyl-2(1H)-quinolinone
rebamipide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 69 percent / sodium / ethanol / 2 h 2: 89 percent / 20 percent hydrochloric acid / 9 h / Heating 3: 49 percent / K2CO3 / acetone; H2O / 2 h View Scheme | |
Multi-step reaction with 5 steps 1.1: magnesium; methyl iodide / tetrahydrofuran; 1,4-dioxane / 10 h / 80 °C / Inert atmosphere; Green chemistry 1.2: 5 h / 70 °C / Inert atmosphere; Green chemistry 2.1: sulfuric acid; potassium hydroxide / Green chemistry 3.1: thionyl chloride / pyridine / 6 h / 70 °C / Inert atmosphere; Green chemistry 4.1: sodium carbonate / 72 h / 50 - 70 °C / Green chemistry 5.1: sulfuric acid / 3 h / 80 °C / Green chemistry View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydroxide / dimethyl sulfoxide; water / 2 h / 20 - 30 °C / Large scale 2: hydrogenchloride; acetic acid / water / 7 h / 130 - 140 °C / Large scale 3: sodium hydroxide / water / 0.5 h / 0 - 10 °C / Large scale View Scheme |
2-acetylamino-2-(ethoxycarbonyl)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionic acid ethyl ester
rebamipide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89 percent / 20 percent hydrochloric acid / 9 h / Heating 2: 49 percent / K2CO3 / acetone; H2O / 2 h View Scheme |
ethanol
4-bromomethyl-2(1H)-quinolinone
diethyl (((4-chlorophenyl)carbonyl)amino)propanedioate
rebamipide
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; sodium ethanolate In water | 7.18 g (92.17%) |
With hydrogenchloride; potassium hydroxide; sodium ethanolate | 7.17 g (92.04%) |
With hydrogenchloride; potassium hydroxide; sodium ethanolate In water | 7.08 g (90.88%) |
With hydrogenchloride; sodium hydroxide; sodium ethanolate | 7.15 g (91.78%) |
With hydrogenchloride; sodium hydroxide; sodium ethanolate In water | 6.7 g (86.0%) |
4-chloro-benzoyl chloride
rebamipide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / chloroform / 0.5 h / 20 °C 1.2: 2 h / 5 - 20 °C 2.1: sodium ethanolate; sodium / ethanol / 1.5 h / 20 °C 2.2: 20 °C 3.1: water; sodium hydroxide / ethanol / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: ammonium hydroxide / 4.5 h / 30 °C / Large scale; Green chemistry 2: sodium carbonate / 72 h / 50 - 70 °C / Green chemistry 3: sulfuric acid / 3 h / 80 °C / Green chemistry View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 4 h / 0 - 25 °C 2: phosphorus pentachloride / toluene / 3 h / 80 °C 3: triethylamine / toluene / 5 h / 70 - 80 °C 4: sodium hydroxide; ethanol / 3 h / 60 - 65 °C View Scheme |
rebamipide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / pyridine / 6 h / 70 °C / Inert atmosphere; Green chemistry 2: sodium carbonate / 72 h / 50 - 70 °C / Green chemistry 3: sulfuric acid / 3 h / 80 °C / Green chemistry View Scheme |
rebamipide
Conditions | Yield |
---|---|
With sulfuric acid at 80℃; for 3h; Green chemistry; |
rebamipide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sulfuric acid; potassium hydroxide / Green chemistry 2: thionyl chloride / pyridine / 6 h / 70 °C / Inert atmosphere; Green chemistry 3: sodium carbonate / 72 h / 50 - 70 °C / Green chemistry 4: sulfuric acid / 3 h / 80 °C / Green chemistry View Scheme |
4-chloro-benzoyl chloride
rebamipide
Conditions | Yield |
---|---|
With sodium hydroxide In water at 0 - 10℃; for 0.5h; Large scale; | 6.85 kg |
3,3-Dimethoxy-N-phenylpropanamide
rebamipide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / dichloromethane / 2 h / 0 - 60 °C / Green chemistry 2: Lindlar's catalyst; ammonia / toluene / 2 h / 90 °C / 375.04 Torr / Inert atmosphere; Autoclave; Green chemistry View Scheme |
N-(benzyloxycarbonyl)aniline
rebamipide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium hydroxide; 5%-palladium/activated carbon; hydrogen / methanol / 2 h / 20 °C / 750.08 Torr / Autoclave; Green chemistry 2: lithium diisopropyl amide / tetrahydrofuran / 5.5 h / 0 - 25 °C / Green chemistry 3: sulfuric acid / dichloromethane / 2 h / 0 - 60 °C / Green chemistry 4: Lindlar's catalyst; ammonia / toluene / 2 h / 90 °C / 375.04 Torr / Inert atmosphere; Autoclave; Green chemistry View Scheme | |
Multi-step reaction with 4 steps 1: sodium hydroxide; 5%-palladium/activated carbon; hydrogen / methanol / 2 h / 20 °C / 750.08 Torr / Autoclave; Green chemistry 2: lithium diisopropyl amide / tetrahydrofuran / 5.5 h / 0 - 25 °C / Green chemistry 3: sulfuric acid / dichloromethane / 2 h / 0 - 60 °C / Green chemistry 4: Lindlar's catalyst; ammonia / toluene / 2 h / 90 °C / 375.04 Torr / Inert atmosphere; Autoclave; Green chemistry View Scheme |
benzoic acid
rebamipide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: triethylamine / toluene / 1 h / 80 - 100 °C / Green chemistry 1.2: 3 h / 10 - 20 °C / Green chemistry 1.3: Green chemistry 2.1: sodium hydroxide; 5%-palladium/activated carbon; hydrogen / methanol / 2 h / 20 °C / 750.08 Torr / Autoclave; Green chemistry 3.1: lithium diisopropyl amide / tetrahydrofuran / 5.5 h / 0 - 25 °C / Green chemistry 4.1: sulfuric acid / dichloromethane / 2 h / 0 - 60 °C / Green chemistry 5.1: Lindlar's catalyst; ammonia / toluene / 2 h / 90 °C / 375.04 Torr / Inert atmosphere; Autoclave; Green chemistry View Scheme | |
Multi-step reaction with 5 steps 1.1: triethylamine / toluene / 1 h / 80 - 100 °C / Green chemistry 1.2: 3 h / 10 - 20 °C / Green chemistry 1.3: Green chemistry 2.1: sodium hydroxide; 5%-palladium/activated carbon; hydrogen / methanol / 2 h / 20 °C / 750.08 Torr / Autoclave; Green chemistry 3.1: lithium diisopropyl amide / tetrahydrofuran / 5.5 h / 0 - 25 °C / Green chemistry 4.1: sulfuric acid / dichloromethane / 2 h / 0 - 60 °C / Green chemistry 5.1: Lindlar's catalyst; ammonia / toluene / 2 h / 90 °C / 375.04 Torr / Inert atmosphere; Autoclave; Green chemistry View Scheme |
aniline
rebamipide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: lithium diisopropyl amide / tetrahydrofuran / 5.5 h / 0 - 25 °C / Green chemistry 2: sulfuric acid / dichloromethane / 2 h / 0 - 60 °C / Green chemistry 3: Lindlar's catalyst; ammonia / toluene / 2 h / 90 °C / 375.04 Torr / Inert atmosphere; Autoclave; Green chemistry View Scheme | |
Multi-step reaction with 3 steps 1: lithium diisopropyl amide / tetrahydrofuran / 5.5 h / 0 - 25 °C / Green chemistry 2: sulfuric acid / dichloromethane / 2 h / 0 - 60 °C / Green chemistry 3: Lindlar's catalyst; ammonia / toluene / 2 h / 90 °C / 375.04 Torr / Inert atmosphere; Autoclave; Green chemistry View Scheme |
N-(p-chlorobenzoyl)-glycine methyl ester
rebamipide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: phosphorus pentachloride / toluene / 3 h / 80 °C 2: triethylamine / toluene / 5 h / 70 - 80 °C 3: sodium hydroxide; ethanol / 3 h / 60 - 65 °C View Scheme |
rebamipide
2-amino-2-hydroxymethyl-1,3-propanediol
2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid tris(hydroxymethyl)aminomethane salt
Conditions | Yield |
---|---|
Stage #1: rebamipide; 2-amino-2-hydroxymethyl-1,3-propanediol In ethanol for 0.5h; Heating / reflux; Stage #2: In ethanol; water Heating / reflux; | 97% |
L-arginine
rebamipide
2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid L-arginine salt
Conditions | Yield |
---|---|
Stage #1: L-arginine; rebamipide In ethanol for 0.5h; Heating / reflux; Stage #2: In ethanol; water Heating / reflux; | 95% |
rebamipide
ethylenediamine
Conditions | Yield |
---|---|
Stage #1: rebamipide; ethylenediamine In ethanol for 0.5h; Heating / reflux; Stage #2: In ethanol; water Product distribution / selectivity; Heating / reflux; | 89% |
Conditions | Yield |
---|---|
at 120℃; for 48h; Autoclave; | 82% |
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; | 80% |
rebamipide
2,2'-iminobis[ethanol]
2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid diethanolamine salt
Conditions | Yield |
---|---|
In ethanol for 0.5h; Heating / reflux; | 76% |
rebamipide
Conditions | Yield |
---|---|
With water; sodium hydroxide In ethanol at 20℃; | 75% |
methanol
rebamipide
methyl 2-(4-chlorobenzoylamino)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionate
Conditions | Yield |
---|---|
In water at 120℃; for 48h; Autoclave; | 75% |
rebamipide
diisopropanolamine
Conditions | Yield |
---|---|
In ethanol for 0.5h; Heating / reflux; | 61% |
1-deoxy-1-(methylamino)-D-glucitol
rebamipide
2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid meglumine salt
Conditions | Yield |
---|---|
Stage #1: 1-deoxy-1-(methylamino)-D-glucitol; rebamipide In water at 50℃; Stage #2: 1-deoxy-1-(methylamino)-D-glucitol With hydrogenchloride In water | 61% |
L-lysine
rebamipide
2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid L-lysine salt
Conditions | Yield |
---|---|
Stage #1: L-lysine; rebamipide In ethanol for 0.5h; Heating / reflux; Stage #2: In ethanol; water Heating / reflux; | 54% |
β-dibutyrin
rebamipide
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide at 0 - 20℃; Inert atmosphere; | 2.2% |
Conditions | Yield |
---|---|
In nitromethane for 120h; Sealed vial; |
Conditions | Yield |
---|---|
In nitromethane for 120h; Sealed vial; |
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In dichloromethane |
rebamipide
cyclohexylmethyl alcohol
Conditions | Yield |
---|---|
With inorganic salt In N,N-dimethyl-formamide at 20 - 80℃; | 0.7 g |
rebamipide
i-pentyl bromide
Conditions | Yield |
---|---|
With inorganic salt In N,N-dimethyl-formamide at 20 - 80℃; | 0.7 g |
Structure of Rebamipide (CAS NO.90098-04-7):
IUPAC Name: 2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1H-quinolin-4-yl)propanoic acid
Empirical Formula: C19H15ClN2O4
Molecular Weight: 370.7864
Index of Refraction: 1.634
Molar Refractivity: 95.07 cm3
Molar Volume: 265.8 cm3
Polarizability: 37.69×10-24cm3
Surface Tension: 58.3 dyne/cm
Density: 1.394 g/cm3
Flash Point: 374.1 °C
Enthalpy of Vaporization: 106.9 kJ/mol
Melting Point: 288-290°C dec.
Boiling Point: 695 °C at 760 mmHg
Vapour Pressure: 2.83E-20 mmHg at 25°C
Physical Appearance: White Powder
Product Categories: Amino Acid Derivatives;Active Pharmaceutical Ingredients;Antiulcerative;Intermediates & Fine Chemicals;Pharmaceuticals;API's
Shows antiulcer activity in rats.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | oral | > 2gm/kg (2000mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 362, 1989. | |
mouse | LD50 | intramuscular | 1353mg/kg (1353mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BLOOD: CHANGES IN SPLEEN | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 362, 1989. |
mouse | LD50 | intravenous | 572mg/kg (572mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 362, 1989. |
mouse | LD50 | subcutaneous | 2637mg/kg (2637mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION KIDNEY, URETER, AND BLADDER: OTHER CHANGES SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 362, 1989. |
mouse | LDLo | oral | > 5gm/kg (5000mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 362, 1989. | |
rabbit | LD50 | oral | > 3gm/kg (3000mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 362, 1989. | |
rat | LD50 | intravenous | 700mg/kg (700mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 362, 1989. |
rat | LDLo | intramuscular | 1gm/kg (1000mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 362, 1989. |
rat | LDLo | oral | 5gm/kg (5000mg/kg) | BEHAVIORAL: FOOD INTAKE (ANIMAL) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 362, 1989. |
rat | LDLo | subcutaneous | 4gm/kg (4000mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 362, 1989. |
Rebamipide , its cas register number is 90098-04-7. It also can be called (+-)-2-(4-Chlorobenzoylamino)-3-(2(1H)-quinolinon-4-yl)propionic acid ; Mucosta ; Proamipide .
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