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90098-04-7

Basic Information
CAS No.: 90098-04-7
Name: Rebamipide
Article Data: 12
Cas Database
Molecular Structure:
Molecular Structure of 90098-04-7 (Rebamipide)
Formula: C19H15ClN2O4
Molecular Weight: 370.792
Synonyms: Mucosta;OPC 12759;Proamipide;Itopride Hydrochloride;
EINECS: 1308068-626-2
Density: 1.394 g/cm3
Melting Point: 288-290 °C dec.
Boiling Point: 695 °C at 760 mmHg
Flash Point: 374.1 °C
Solubility: N/A
Appearance: white powder
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 99.26000
LogP: 2.99810
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%)
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Chemistry

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

Uses

Shows antiulcer activity in rats.

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.

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 .