142613-14-7

Basic information

• Product Name: Propanoic acid, 3-(ethylphenylamino)-3-oxo-, methyl ester
• CAS NO: 142613-14-7
• Molecular Formula: C12H15NO3
• Molecular Weight: 221.256
• Mol File: 142613-14-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Propanoic acid, 3-(ethylphenylamino)-3-oxo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 3-(ethylphenylamino)-3-oxo-, methyl ester(142613-14-7)
• EPA Substance Registry System: Propanoic acid, 3-(ethylphenylamino)-3-oxo-, methyl ester(142613-14-7)

Safety Data

• Hazardous Substances Data: 142613-14-7(Hazardous Substances Data)

Upstream product

• 37517-81-0 3-chloro-3-oxopropanoic acid methyl ester 
• 103-69-5 N-ethyl-N-phenylamine 
• 16695-14-0 Malonic acid monomethyl ester 

Downstream Products

• 142612-52-0 N-ethyl-N-phenyl-α-(methoxycarbonyl)-α-diazoacetamide 
• 61-28-9 1-ethyl-1,3-dihydro-2H-indol-2-one 
• 142612-64-4 trans-3-carbomethoxy-4-methyl-1-phenyl-2-azetidinone 
• 248281-84-7 laquinimod 
• 118081-77-9 3-(Ethyl(phenyl)amino)-3-oxopropanoic acid 
• 1379595-99-9 methyl 2-chloro-6-[[3-(ethyl(phenyl)amino)-3-oxopropanoyl]methylamino]benzoate 

Relevant articles and documents

Development of a practical and reliable synthesis of laquinimod

Laquinimod(5-chloro-1,2-dihydro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl- 3-quinoline carboxamide) is a drug candidate for treatment of Multiple Sclerosis. A short and industrially feasible process for the preparation of laquinimod starting from 2-amino-6-chlorobenzoic acid, in essentially four steps, is discussed. The key step is a novel reaction in which a methyl ester is converted to an amide in very high yield and with excellent purity. The present article elucidates the scale-up process along with safety aspects and the impurity profiles of the intermediates and product. Initial laboratory conditions are described as well as the changes made on transfer to pilot-plant scale.

INTERMEDIATE COMPOUNDS AND PROCESSES FOR THE PREPARATION OF QUINOLINE DERIVATIVES SUCH AS LAQUINIMOD SODIUM

The present invention relates to processes for the preparation of quinoline-3 -carboxamide derivatives, such as sodium 5-chloro-3-(ethylphenylcarbamoyl)-l-methyl-2- oxo-l,2-dihydroquinolin-4-olate (Laquinimod sodium). The present invention further relates to intermediates formed in such processes.

Dirhodium Tetraacetate Catalyzed Carbon-Hydrogen Insertion Reaction in N-Substituted α-Carbomethoxy-α-diazoacetanilides and Structural Analogues. Substituent and Conformational Effects

A series of acyclic α-carbomethoxy-α-diazoacetanilides with different N-substituents, 5a-k, was prepared and the rhodium(II) acetate catalyzed reaction studied.It was found that the rhodium carbenoid reaction with these compounds occurred only at the N-substituent; when the N-substituent is a propargyl group, rhodium carbenoid addition to the triple bond is favored, resulting, ultimately, in the formation of a bicyclic furan derivative 8.With an N-(tert-butyloxycarbonyl)methyl substituent, interception of the rhodium carbenoid by the ester carbonyl oxygen occurred preferentially to give, eventually, 1,4-oxazine derivatives 9 and 9'.For N'-alkyl substituents, rhodium carbenoid carbon-hydrogen (C-H) insertion into the alkyl group to give the 2-azetidinone and/or 2-pyrrolidinone derivatives was observed.The chemoselectivity of the rhodium carbenoid C-H insertion can be altered by the use of the α-acetyl and α-phenylsulfonyl substituents.In these cases, exclusive C-H insertion at the N-aryl moiety resulted to give 2(3H)-indolinone products.However, the α-substituent effect on the chemoselectivity of the insertion reaction is easily overridden by conformational effects about the amide N-C(O) bond as revealed by the insertion reaction of the conformationally rigid compounds 20a-c.The α-substituent effects are reestablished when conformational rigidity is removed, as exemplified by the rhodium carbenoid insertion reactions of compounds 29a, b.