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90098-04-7

90098-04-7

Identification

  • Product Name:Rebamipide

  • CAS Number: 90098-04-7

  • EINECS:1308068-626-2

  • Molecular Weight:370.792

  • Molecular Formula: C19H15ClN2O4

  • HS Code:29337900

  • Mol File:90098-04-7.mol

Synonyms:Mucosta;OPC 12759;Proamipide;Itopride Hydrochloride;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:Rebamipide
  • Packaging:10g
  • Price:$ 235
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Rebamipide >98.0%(HPLC)
  • Packaging:1g
  • Price:$ 15
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Rebamipide >98.0%(HPLC)
  • Packaging:5g
  • Price:$ 43
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Rebamipide >98.0%(HPLC)
  • Packaging:25g
  • Price:$ 127
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Rebamipide hydrate ≥98% (HPLC), powder
  • Packaging:25mg
  • Price:$ 277
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Rebamipide hydrate ≥98% (HPLC), powder
  • Packaging:5mg
  • Price:$ 69.4
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:Rebamipide
  • Packaging:100 mg
  • Price:$ 90
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  • Manufacture/Brand:Crysdot
  • Product Description:Rebamipide 98+%
  • Packaging:5g
  • Price:$ 180
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  • Manufacture/Brand:ChemScene
  • Product Description:Rebamipide 99.88%
  • Packaging:5g
  • Price:$ 168
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  • Manufacture/Brand:ChemScene
  • Product Description:Rebamipide 99.88%
  • Packaging:1g
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Relevant articles and documentsAll total 12 Articles be found

Preparation method of rebamipide bulk drug

-

, (2021/08/14)

The invention discloses a preparation method of a rebamipide bulk drug. The preparation method comprises the following steps: 1, preparing a crude product of the rebamipide bulk drug: preparing the crude product of the rebamipide bulk drug by utilizing a compound III and 4-chlorobenzoyl chloride; and 2, purifying the rebamipide bulk drug. The compound III is prepared from a compound II, deionized water and concentrated hydrochloric acid, the compound II is prepared from a compound I, glacial acetic acid and concentrated hydrochloric acid, and the compound I is prepared from diethyl acetamidomalonate and 4-bromomethylquinolone. A process control method is utilized, impurities in the synthesized compound I, impurities in the synthesized compound II and impurities in the synthesized compound III are respectively subjected to impurity removal and purification by a common purification method, and the purity of the rebamipide bulk drug is improved in combination with a method for crystallizing and purifying the crude product of the rebamipide bulk drug.

New process for synthesizing rebamipide

-

Paragraph 0013; 0029; 0036-0037; 0038; 0045-0046, (2020/12/30)

The invention discloses a novel process for synthesizing rebamipide. The novel process comprises the following steps: adopting glycine methyl ester as a starting raw material, then performing amidation and chlorination to obtain chloroimide intermediate, enabling the chloroimide intermediate to react with bromomethylquinolone, and hydrolyzing to obtain the rebamipide. The novel process has the advantages that the starting raw material is low in price and easy to obtain, the reaction yield is high, the industrialization is easy to realize and the like.

Green and efficient preparation method of rebamipide

-

, (2018/09/12)

The invention belongs to the technical field of medical synthesis and in particular relates to a green and efficient preparation method of rebamipide. The synthesis method provided by the invention has a green and simple route and the price of raw materials is low, so that industrial production is easy to realize. The invention further discloses a novel method for preparing aniline from benzoic acid.

Magic Bullet! Rebamipide, a Superior Anti-ulcer and Ophthalmic Drug and Its Large-Scale Synthesis in a Single Organic Solvent via Process Intensification Using Krapcho Decarboxylation

Babu, Prashanth Kumar,Bodireddy, Mohan Reddy,Puttaraju, Reshma Choudlu,Vagare, Dnyaneshwar,Nimmakayala, Raghu,Surineni, Naresh,Gajula, Madhusudana Rao,Kumar, Pramod

, p. 773 - 779 (2018/06/11)

Rebamipide (1) is a superior drug compared to existing drugs for use in healing of peptic ulcers, gastrointestinal bleeding, and dyspepsia. It is also useful as an ophthalmic drug for the treatment of dry eye syndrome. Process intensification for its synthesis was achieved by (i) averting uncontrollable frothing using Krapcho decarboxylation instead of conventional acid hydrolysis, where uncontrollable frothing became chaotic, (ii) minimizing organic waste generation by using a single organic solvent, and (iii) avoiding anti-foaming agents (n-octanol, acetophenone) and acetic acid. With these trifling modifications, the overall yield of active pharmaceutical ingredient (API) was ≥83% with excellent purity (≥99.89%), and the process meets the metrics of "green" chemistry with an E-factor = 11.5. The developed hassle-free commercial process is viable for multi-kilogram synthesis of Rebamipide (1) as the key step, Krapcho decarboxylation is safe to run at 130-140 °C in DMSO, and it was proved to be effective by differential scanning calorimetry thermal screening studies. The characterization data of intermediates, process-related impurities, and API are reported. The carryover and process-related impurities were controlled efficiently. The present work can enhance the scope and worldwide adoptability of Rebamipide (1), which is currently limited to Asian countries.

A synthesis process of fluorinated

-

, (2018/07/30)

The present invention discloses a process for synthesizing a fluorinated, the specific synthetic process are as follows: ammonia added in a reaction vessel, then drip to the wherein the dripped into the 4 - chlorobenzene chloride, to obtain 4 - chlorobenzene formyl ammonia; format after the reaction will be carried out with the formic acid reaction product 1; the product 1, to carry out addition reaction product 2; then the product 2 with chloro after 4 - chlorobenzene formyl ammonia reaction to obtain the product 3; the product 3 added in a reaction vessel, then adding the mass fraction is 60% sulfuric acid solution, heating to 80 °C stirring reaction 3 h, to obtain the product 2 - (4 - chlorophenyl formamido) - 3 - [2 (1 H) - quinolinone - 4] propionic acid. In the process of synthesis of the present invention through the form reaction, nucleophilic addition and the substitution reaction preparation, the production cost is low, and a high yield of product, synthetic condition is simple, can be suitable for large-scale production.

Process route upstream and downstream products

Process route

2(1H)-quinolinon-4-ylpropionic acid
71028-92-7

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

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

Conditions
Conditions Yield
With Lindlar's catalyst; ammonia; In toluene; at 90 ℃; for 2h; under 375.038 Torr; Reagent/catalyst; Inert atmosphere; Autoclave; Green chemistry;
89%
2-amino-3-[6-bromo-2(1H)-quinolon-4-yl]propionic acid
889573-80-2

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

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

2-amino-3-<2-(1H)-quinolinon-4-yl>propionic acid hydrochloride
4876-14-6,132210-24-3

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

Conditions
Conditions Yield
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;
4-chloro-benzoyl chloride; With sodium hydroxide; In water; acetone; at 0 ℃;
With hydrogenchloride; In water; acetone;
96.2%
4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

2‐amino‐3‐[2(1H)‐quinolinon‐4‐yl]propionic acid
5162-90-3

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

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

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

Conditions
Conditions Yield
With water; sodium hydroxide; In ethanol; Reflux;
94%
C<sub>20</sub>H<sub>16</sub>Cl<sub>2</sub>N<sub>2</sub>O<sub>3</sub>

C20H16Cl2N2O3

Conditions
Conditions Yield
With ethanol; sodium hydroxide; at 60 - 65 ℃; for 3h;
93%
4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

2-amino-3-<2-(1H)-quinolinon-4-yl>propionic acid hydrochloride
4876-14-6,132210-24-3

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

Conditions
Conditions Yield
With potassium carbonate; In water; acetone; for 2h;
49%
2-amino-3-<2-(1H)-quinolinon-4-yl>propionic acid hydrochloride; With sodium hydroxide; In N,N-dimethyl acetamide; at 0 ℃; for 0.166667h;
4-chloro-benzoyl chloride; In N,N-dimethyl acetamide; toluene; at 3 ℃; for 5h;
With acetic acid; In methanol; N,N-dimethyl acetamide; toluene; at 75 ℃;
ethanol
64-17-5

ethanol

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

4-bromomethyl-2(1H)-quinolinone

diethyl (((4-chlorophenyl)carbonyl)amino)propanedioate
81918-01-6

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

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%)
C<sub>19</sub>H<sub>14</sub>ClN<sub>3</sub>O<sub>2</sub>

C19H14ClN3O2

Conditions
Conditions Yield
With sulfuric acid; at 80 ℃; for 3h; Green chemistry;
2-amino-3-[2(1H)-quinolinone-4-yl]propionic acid dihydrochloride dihydrate
914769-50-9

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

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

Conditions
Conditions Yield
2-amino-3-[2(1H)-quinolinone-4-yl]propionic acid dihydrochloride dihydrate; 4-chloro-benzoyl chloride; With sodium hydroxide; In water; acetone; at 0 ℃;
With hydrogenchloride; In water; acetone;
96.9%
4-bromomethyl-2(1H)-quinolinone
4876-10-2

4-bromomethyl-2(1H)-quinolinone

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
With hydrogenchloride; sodium; potassium carbonate; In ethanol; water; acetone;
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
With thionyl chloride; sulfuric acid; sodium carbonate; magnesium; potassium hydroxide; methyl iodide; In tetrahydrofuran; 1,4-dioxane; pyridine;
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
With hydrogenchloride; acetic acid; sodium hydroxide; In water; dimethyl sulfoxide;
Multi-step reaction with 4 steps
1.1: sodium methylate; ethanol / 0.42 h / 30 °C
1.2: 1.5 h / 78 °C
1.3: 2.5 h / 65 - 80 °C
2.1: acetic acid; hydrogenchloride / water / 8 h / 103 °C
3.1: hydrogenchloride / water / 105 °C
4.1: sodium hydroxide / N,N-dimethyl acetamide / 0.17 h / 0 °C
4.2: 5 h / 3 °C
4.3: 75 °C
With hydrogenchloride; ethanol; sodium methylate; acetic acid; sodium hydroxide; In N,N-dimethyl acetamide; water;

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