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Rebamipide

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Name

Rebamipide

EINECS 1308068-626-2
CAS No. 90098-04-7 Density 1.394 g/cm3
PSA 99.26000 LogP 2.99810
Solubility Melting Point 288-290 °C dec.
Formula C19H15ClN2O4 Boiling Point 695 °C at 760 mmHg
Molecular Weight 370.07 Flash Point 374.1 °C
Transport Information Appearance white powder
Safety Risk Codes
Molecular Structure Molecular Structure of 90098-04-7 (Rebamipide) Hazard Symbols
Synonyms

Mucosta;OPC 12759;Proamipide;Itopride Hydrochloride;

 

Rebamipide Synthetic route

2-amino-3-[2(1H)-quinolinone-4-yl]propionic acid dihydrochloride dihydrate

122-01-0

4-chloro-benzoyl chloride

90098-04-7

rebamipide

Conditions
ConditionsYield
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%
889573-80-2

2-amino-3-[6-bromo-2(1H)-quinolon-4-yl]propionic acid

122-01-0

4-chloro-benzoyl chloride

4876-14-6

2-amino-3-<2-(1H)-quinolinon-4-yl>propionic acid hydrochloride

90098-04-7

rebamipide

Conditions
ConditionsYield
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%
1028268-32-7

ethyl 2-(4-chlorobenzamido)-2-ethoxyoxo-3-[2-(1H)-quinolin-4-yl]propionate

90098-04-7

rebamipide

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol Reflux;94%

C20H16Cl2N2O3

90098-04-7

rebamipide

Conditions
ConditionsYield
With ethanol; sodium hydroxide at 60 - 65℃; for 3h;93%
71028-92-7

2(1H)-quinolinon-4-ylpropionic acid

122-01-0

4-chloro-benzoyl chloride

90098-04-7

rebamipide

Conditions
ConditionsYield
With Lindlar's catalyst; ammonia In toluene at 90℃; under 375.038 Torr; for 2h; Reagent/catalyst; Inert atmosphere; Autoclave; Green chemistry;89%
122-01-0

4-chloro-benzoyl chloride

5162-90-3

2‐amino‐3‐[2(1H)‐quinolinon‐4‐yl]propionic acid

90098-04-7

rebamipide

Conditions
ConditionsYield
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;
122-01-0

4-chloro-benzoyl chloride

4876-14-6

2-amino-3-<2-(1H)-quinolinon-4-yl>propionic acid hydrochloride

90098-04-7

rebamipide

Conditions
ConditionsYield
With potassium carbonate In water; acetone for 2h;49%
4876-10-2

4-bromomethyl-2(1H)-quinolinone

90098-04-7

rebamipide

Conditions
ConditionsYield
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
4900-38-3

2-acetylamino-2-(ethoxycarbonyl)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionic acid ethyl ester

90098-04-7

rebamipide

Conditions
ConditionsYield
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
64-17-5

ethanol

4876-10-2

4-bromomethyl-2(1H)-quinolinone

81918-01-6

diethyl (((4-chlorophenyl)carbonyl)amino)propanedioate

90098-04-7

rebamipide

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium ethanolate In water7.18 g (92.17%)
With hydrogenchloride; potassium hydroxide; sodium ethanolate7.17 g (92.04%)
With hydrogenchloride; potassium hydroxide; sodium ethanolate In water7.08 g (90.88%)
With hydrogenchloride; sodium hydroxide; sodium ethanolate7.15 g (91.78%)
With hydrogenchloride; sodium hydroxide; sodium ethanolate In water6.7 g (86.0%)
122-01-0

4-chloro-benzoyl chloride

90098-04-7

rebamipide

Conditions
ConditionsYield
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

C12H10N2O2

90098-04-7

rebamipide

Conditions
ConditionsYield
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

C19H14ClN3O2

90098-04-7

rebamipide

Conditions
ConditionsYield
With sulfuric acid at 80℃; for 3h; Green chemistry;

C11H9NO2

90098-04-7

rebamipide

Conditions
ConditionsYield
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

2-amino-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoic acid dihydrochloride

122-01-0

4-chloro-benzoyl chloride

90098-04-7

rebamipide

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 10℃; for 0.5h; Large scale;6.85 kg
122347-19-7

3,3-Dimethoxy-N-phenylpropanamide

90098-04-7

rebamipide

Conditions
ConditionsYield
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
3422-02-4

N-(benzyloxycarbonyl)aniline

90098-04-7

rebamipide

Conditions
ConditionsYield
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
65-85-0

benzoic acid

90098-04-7

rebamipide

Conditions
ConditionsYield
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
62-53-3

aniline

90098-04-7

rebamipide

Conditions
ConditionsYield
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
59893-99-1

N-(p-chlorobenzoyl)-glycine methyl ester

90098-04-7

rebamipide

Conditions
ConditionsYield
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
90098-04-7

rebamipide

77-86-1

2-amino-2-hydroxymethyl-1,3-propanediol

861243-12-1

2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid tris(hydroxymethyl)aminomethane salt

Conditions
ConditionsYield
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%
74-79-3

L-arginine

90098-04-7

rebamipide

861243-10-9

2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid L-arginine salt

Conditions
ConditionsYield
Stage #1: L-arginine; rebamipide In ethanol for 0.5h; Heating / reflux;
Stage #2: In ethanol; water Heating / reflux;
95%
90098-04-7

rebamipide

107-15-3

ethylenediamine

2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid 1/2 ethylenediamine salt

Conditions
ConditionsYield
Stage #1: rebamipide; ethylenediamine In ethanol for 0.5h; Heating / reflux;
Stage #2: In ethanol; water Product distribution / selectivity; Heating / reflux;
89%
67-56-1

methanol

90098-04-7

rebamipide

C19H15ClN2O4*CH4O

Conditions
ConditionsYield
at 120℃; for 48h; Autoclave;82%
64-17-5

ethanol

90098-04-7

rebamipide

C19H14ClN2O4(1-)*Na(1+)*C2H6O

Conditions
ConditionsYield
With sodium hydroxide at 20℃;80%
90098-04-7

rebamipide

111-42-2

2,2'-iminobis[ethanol]

861243-13-2

2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid diethanolamine salt

Conditions
ConditionsYield
In ethanol for 0.5h; Heating / reflux;76%
90098-04-7

rebamipide

C19H13ClN2O4(2-)*2Na(1+)*4H2O

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 20℃;75%
67-56-1

methanol

90098-04-7

rebamipide

90098-38-7

methyl 2-(4-chlorobenzoylamino)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionate

Conditions
ConditionsYield
In water at 120℃; for 48h; Autoclave;75%
90098-04-7

rebamipide

110-97-4

diisopropanolamine

2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid diisopropanolamine salt

Conditions
ConditionsYield
In ethanol for 0.5h; Heating / reflux;61%
6284-40-8

1-deoxy-1-(methylamino)-D-glucitol

90098-04-7

rebamipide

861243-15-4

2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid meglumine salt

Conditions
ConditionsYield
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%
56-87-1

L-lysine

90098-04-7

rebamipide

847165-02-0

2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid L-lysine salt

Conditions
ConditionsYield
Stage #1: L-lysine; rebamipide In ethanol for 0.5h; Heating / reflux;
Stage #2: In ethanol; water Heating / reflux;
54%
90098-04-7

rebamipide

3-((2-(4-chlorobenzamido)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoyl)oxy)propane-1,2-diyl dibutyrate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide at 0 - 20℃; Inert atmosphere;2.2%
98-92-0

nicotinamide

90098-04-7

rebamipide

rebamipide nicotinamide

Conditions
ConditionsYield
In nitromethane for 120h; Sealed vial;
89-86-1

4-hydroxysalicylic acid

90098-04-7

rebamipide

rebamipide 2,4-dihydroxybenzoic acid

Conditions
ConditionsYield
In nitromethane for 120h; Sealed vial;
88192-19-2

3-azidopropylamine

90098-04-7

rebamipide

C22H21ClN6O3

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole In dichloromethane
90098-04-7

rebamipide

100-49-2

cyclohexylmethyl alcohol

cyclohexylmethyl 2-(4-chlorobenzoylamino)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionate

Conditions
ConditionsYield
With inorganic salt In N,N-dimethyl-formamide at 20 - 80℃;0.7 g
90098-04-7

rebamipide

107-82-4

i-pentyl bromide

3-methylbutyl 2-(4-chlorobenzoylamino)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionate

Conditions
ConditionsYield
With inorganic salt In N,N-dimethyl-formamide at 20 - 80℃;0.7 g

Rebamipide Chemical Properties

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

Rebamipide Uses

Shows antiulcer activity in rats.

Rebamipide Toxicity Data With Reference

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 Specification

  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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