CAS No.90098-04-7,Rebamipide Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	90098-04-7
Name:	Rebamipide
Article Data:	12

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
Appearance:	white powder
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

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%

: 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

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%

...Expand

: 1028268-32-7
ethyl 2-(4-chlorobenzamido)-2-ethoxyoxo-3-[2-(1H)-quinolin-4-yl]propionate

: 90098-04-7
rebamipide

Conditions

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

: C20H16Cl2N2O3

: 90098-04-7
rebamipide

Conditions

Conditions	Yield
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

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%

: 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

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;

: 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

Conditions	Yield
With potassium carbonate In water; acetone for 2h;	49%

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 90098-04-7
rebamipide

Conditions

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

: 4900-38-3
2-acetylamino-2-(ethoxycarbonyl)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionic acid ethyl ester

: 90098-04-7
rebamipide

Conditions

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

: 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

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%)

...Expand

Raw Materials

122-01-0

4876-10-2

64-17-5

81918-01-6

4876-14-6

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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 .