142612-52-0

Basic information

• Product Name: Propanoic acid, 2-diazo-3-(ethylphenylamino)-3-oxo-, methyl ester
• CAS NO: 142612-52-0
• Molecular Formula: C12H13N3O3
• Molecular Weight: 247.254
• Mol File: 142612-52-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Propanoic acid, 2-diazo-3-(ethylphenylamino)-3-oxo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 2-diazo-3-(ethylphenylamino)-3-oxo-, methyl ester(142612-52-0)
• EPA Substance Registry System: Propanoic acid, 2-diazo-3-(ethylphenylamino)-3-oxo-, methyl ester(142612-52-0)

Safety Data

• Hazardous Substances Data: 142612-52-0(Hazardous Substances Data)

Upstream product

• 103-69-5 N-ethyl-N-phenylamine 
• 142613-14-7 methyl 3-(N-ethyl-N-phenylamino)-3-oxopropionate 

Downstream Products

• 142612-64-4 trans-3-carbomethoxy-4-methyl-1-phenyl-2-azetidinone 
• 61-28-9 1-ethyl-1,3-dihydro-2H-indol-2-one 

Relevant articles and documents

Palladium-catalysed intramolecular carbenoid insertion of α-diazo-α-(methoxycarbonyl)acetanilides for oxindole synthesis

A novel, selective palladium-catalysed carbenoid C(aryl)-H insertion of α-diazo-α-(methoxycarbonyl)acetanilides leading to oxindoles is described.

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.