16899-81-3

Basic information

• Product Name: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride
• Synonyms: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride;U 12844A;Ethanone,1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino]-, hydrochloride (1:1);1-(3,4-Dihydroxyphenyl)-2-[(1-methylethyl)amino]ethanone hydrochloride;Isoprenaline impurity A
• CAS NO: 16899-81-3
• Molecular Formula: C₁₁H₁₅NO₃*ClH
• Molecular Weight: 245.704
• EINECS: 240-943-7
• Mol File: 16899-81-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 255-257℃
• Boiling Point: 409.7°Cat760mmHg
• Flash Point: 201.6°C
• Appearance: /
• Density: 1.185g/cm³
• Vapor Pressure: 2.69E-07mmHg at 25°C
• CAS DataBase Reference: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride(16899-81-3)
• EPA Substance Registry System: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride(16899-81-3)

Safety Data

• Hazardous Substances Data: 16899-81-3(Hazardous Substances Data)

Usage

Uses

1-(3,4-Dihydroxyphenyl)-2-[(1-methylethyl)amino]-ethanone is an impurity of Isoprenaline (I874200, HCl salt) which is non-selective beta-adrenergic agonist. Isoprenaline is used in the treatment of bradycardia.

Preparation

Obtained by condensation of a-chloro-3,4- dihydroxy-acetophenone with isopropylamine in isopropanol at 65–70°. The amino ketone which separated was treated with concentrated hydrochloric acid (54%), (46%).

InChI:InChI=1/C11H15NO3.ClH/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8;/h3-5,7,12-14H,6H2,1-2H3;1H

Upstream product

• 99-40-1 2-chloro-3',4'-dihydroxyacetophenone 
• 120-80-9 benzene-1,2-diol 
• 75-29-6 isopropyl chloride 
• 499-61-6 arterenone 
• 75-31-0 isopropylamine 

Downstream Products

• 30416-01-4 C₂₇H₂₇NO₅*C₂HF₃O₂ 
• 98634-90-3 3',4'-diacetoxy-2-(isopropylamino)acetophenone hydrochloride 
• 18810-21-4 (+)-Isoproterenol hydrochloride 
• 51-30-9 isoproterenol hydrochloride 
• 55508-67-3 3,4-O-diacetylisoproterenol hydrochloride 
• 30416-00-3 3,4-Bis-(p-toluyloxy)phenylisopropylaminomethylketon 

Relevant articles and documents

Preparation method of isoproterenol hydrochloride

The invention relates to the technical field of raw material medicine synthesis, in particular to a preparation method of isoproterenol hydrochloride. According to the preparation method, water, N, N-dimethylformamide or an aqueous solution of N, N-dimethylformamide is used as a solvent, borohydride is used as a reducing agent to carry out reduction reaction on isopropyladrenolone or salt thereof, the reaction conditions are mild, compared with a conventional hydrogenation reduction process, the production safety is remarkably improved, the production cost is greatly reduced, the usage amount of borohydride is small, and the environmental protection is improved to a certain extent. The product obtained by the preparation method is very high in purity, is suitable for industrial production of isoprenaline hydrochloride as a medicine raw material medicine product, and can effectively avoid toxic and side effects caused by impurities.

Method for preparing isoproterenol hydrochloride

The invention relates to a method for preparing isoproterenol hydrochloride. The method comprises the following steps: (1) preparation of 2-amino-1-(3, 4-dihydroxy phenyl)-ethanone; (2) preparation of isoproterenol ketone hydrochloride; and (3) preparation of isoproterenol hydrochloride. The method disclosed by the invention adopts a reaction system of glycine and zinc chloride instead of a reaction system of monochloro acetic acid and phosphorus oxychloride, so that the method has the advantages that the environmental protection cost is reduced; the reaction yield is increased; the industrial production is benefited; the reaction condition is mild; the catalyst quantity is little; and the process is simple. Compared with conventional synthetic processes, the method disclosed by the invention has obvious economic benefit and environmental benefit.