71510-95-7

Usage

Uses

Used in Organic Synthesis:
Ethyl-N-methyl malonamide is utilized as a reagent in organic synthesis for its ability to facilitate various chemical reactions, contributing to the formation of a wide array of organic compounds.
Used as a Ligand in Coordination Complexes:
In the field of coordination chemistry, Ethyl-N-methyl malonamide is employed as an effective ligand, playing a crucial role in the synthesis of coordination complexes, which are essential for numerous applications in areas such as catalysis, materials science, and medicinal chemistry.
Used as a Precursor in Pharmaceutical Synthesis:
Ethyl-N-methyl malonamide serves as a precursor in the synthesis of pharmaceuticals, enabling the development of new drugs with potential therapeutic benefits.
Used as a Precursor in Agrochemical Synthesis:
Similarly, in agrochemical production, Ethyl-N-methyl malonamide is used as a precursor to create compounds that can be employed in the agricultural sector for pest control and crop protection.
Used in the Synthesis of Other Organic Compounds:
Beyond its applications in pharmaceuticals and agrochemicals, Ethyl-N-methyl malonamide is also used as a precursor in the synthesis of a variety of other organic compounds, further expanding its utility in the field of organic chemistry.

InChI:InChI=1/C6H11NO3/c1-3-10-6(9)4-5(8)7-2/h3-4H2,1-2H3,(H,7,8)

Synthetic route

2-carboethoxy-N-methyl-acetamide (71510-95-7) + C14H13FN2O → (3S,4R)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione (188302-25-2)

Conditions	Yield
Stage #1: C14H13FN2O With C31H44N4O4; ytterbium(III) triflate In dichloromethane at 35℃; for 0.5h; Molecular sieve; Inert atmosphere; Stage #2: 2-carboethoxy-N-methyl-acetamide With triethylamine In dichloromethane at 40℃; for 72h; Reagent/catalyst; Solvent; Concentration; Inert atmosphere; Molecular sieve; stereoselective reaction;	90%

2-carboethoxy-N-methyl-acetamide (71510-95-7) + p-fluorocinnamoyl-3,5-dimethyl-1H-pyrazole → (3R,4S)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione

Conditions	Yield
Stage #1: 2-carboethoxy-N-methyl-acetamide; p-fluorocinnamoyl-3,5-dimethyl-1H-pyrazole With C32H46N4O4; ytterbium(III) triflate In toluene at 35℃; for 0.333333h; Stage #2: With triethylamine In toluene at 30 - 50℃; Reagent/catalyst; Solvent;	85.5%

2-carboethoxy-N-methyl-acetamide (71510-95-7) → 2-carboisopropoxy-N-methyl-acetamide (323203-14-1)

Conditions	Yield
In isopropyl alcohol; mineral oil	82%
In isopropyl alcohol; mineral oil	82%

2-carboethoxy-N-methyl-acetamide (71510-95-7) + 3-[3-(4-fluorophenyl)acryloyl]-(R)-4-phenyl-oxazolidin-2-one → (3S,4R)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione (188302-25-2)

Conditions	Yield
Stage #1: 2-carboethoxy-N-methyl-acetamide With sodium hydride In dimethyl sulfoxide at 20℃; Inert atmosphere; Stage #2: 3-[3-(4-fluorophenyl)acryloyl]-(R)-4-phenyl-oxazolidin-2-one In dimethyl sulfoxide at 20℃; Inert atmosphere;	80%

2-carboethoxy-N-methyl-acetamide (71510-95-7) + 4-nitrophenyl 3-phenylprop-2-ynoate → (Z)-ethyl 5-benzylidene-2-(methylamino)-4-oxo-4,5-dihydrofuran-3-carboxylate

Conditions	Yield
With 1,3-bis(mesityl)imidazolium chloride; N-ethyl-N,N-diisopropylamine; lithium chloride In acetonitrile at 65℃; for 10h; Reagent/catalyst; Molecular sieve; Inert atmosphere; regioselective reaction;	77%

2-carboethoxy-N-methyl-acetamide (71510-95-7) + 1,2-diamino-benzene (95-54-5) → 4-Methylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one (91598-13-9)

Conditions	Yield
With trichlorophosphate at 110℃; for 4h;	59.1%

2-carboethoxy-N-methyl-acetamide (71510-95-7) + 1,2,4-triaminopyridin-1-ium 2,4,6-trimethylbenzenesulfonate → 2-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-N-methylacetamide

Conditions	Yield
With sodium hydroxide In methanol Reflux;	39.4%

2-carboethoxy-N-methyl-acetamide (71510-95-7) + 1,2,4-triamino-4-bromopyridin-1-ium-2,4,6-trimethylbenzenesulfonate → 2-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-N-methylacetamide

Conditions	Yield
With sodium hydroxide In methanol Reflux;	39.4%

2-carboethoxy-N-methyl-acetamide (71510-95-7) → ethyl 2-bromo-3-(methylamino)-3-oxopropanoate

Conditions	Yield
With sodium hydrogen sulfate; N-Bromosuccinimide In tetrahydrofuran at 0℃; Inert atmosphere;	20%

2-carboethoxy-N-methyl-acetamide (71510-95-7) + 4-fluorobenzaldehyde (459-57-4) → trans 3-ethoxycarbonyl-4-(4'-fluorophenyl)-N-methyl-piperidine-2,6-dione (202534-94-9)

Conditions	Yield
With sodium methylate; acetic acid In water; ethyl acetate
With sodium methylate; acetic acid In water; ethyl acetate

2-carboethoxy-N-methyl-acetamide (71510-95-7) + 3-phenyl-propenal (104-55-2) → C15H19NO4 + C15H19NO4 (323203-12-9)

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; potassium acetate In 2,2,2-trifluoroethanol at 20℃; optical yield given as %ee; enantioselective reaction;

(E)-3-phenylpropenal (14371-10-9) + 2-carboethoxy-N-methyl-acetamide (71510-95-7) → (3R,4S,6S)-ethyl 6-hydroxy-1-methyl-2-oxo-4-phenylpiperidine-3-carboxylate

Conditions	Yield
With (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; potassium acetate In 2,2,2-trifluoroethanol at 20℃; for 14h; optical yield given as %ee; enantioselective reaction;

3-(4-nitrophenyl)-propenal (49678-08-2) + 2-carboethoxy-N-methyl-acetamide (71510-95-7) → (3S,4R,6R)-ethyl 6-hydroxy-1-methyl-4-(4-nitrophenyl)-2-oxopiperidine-3-carboxylate (1345157-71-2)

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; potassium acetate In 2,2,2-trifluoroethanol at 20℃; for 14h; optical yield given as %ee; enantioselective reaction;

2-carboethoxy-N-methyl-acetamide (71510-95-7) + 4-chlorocinnamaldehyde (1075-77-0) → (3S,4R,6R)-ethyl 4-(4-chlorophenyl)-6-hydroxy-1-methyl-2-oxopiperidine-3-carboxylate (1345157-65-4) + ethyl 4-(4-chlorophenyl)-6-hydroxy-1-methyl-2-oxopiperidine-3-carboxylate

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; potassium acetate In 2,2,2-trifluoroethanol at 20℃; for 14h; optical yield given as %de; enantioselective reaction;

2-carboethoxy-N-methyl-acetamide (71510-95-7) + trans-4-bromocinnamaldehyde (49678-04-8) → (3S,4R,6R)-ethyl 4-(4-bromophenyl)-6-hydroxy-1-methyl-2-oxopiperidine-3-carboxylate (1345157-68-7) + ethyl 4-(4-bromophenyl)-6-hydroxy-1-methyl-2-oxopiperidine-3-carboxylate

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; potassium acetate In 2,2,2-trifluoroethanol at 20℃; for 14h; optical yield given as %de; enantioselective reaction;

2-carboethoxy-N-methyl-acetamide (71510-95-7) + 3-(4-fluoro-phenyl)-propenal (51791-26-5, 24654-55-5) → ethyl 4-(4-fluorophenyl)-6-hydroxy-1-methyl-2-oxopiperidine-3-carboxylate + ethyl 4-(4-fluorophenyl)-6-hydroxy-1-methyl-2-oxopiperidine-3-carboxylate

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; potassium acetate In 2,2,2-trifluoroethanol at 20℃; for 14h; optical yield given as %de; enantioselective reaction;

2-carboethoxy-N-methyl-acetamide (71510-95-7) + 3-(4-methylphenyl)acrylaldehyde (1504-75-2) → (3S,4R,6R)-ethyl 6-hydroxy-1-methyl-2-oxo-4-p-tolylpiperidine-3-carboxylate (1345157-60-9) + ethyl 6-hydroxy-1-methyl-2-oxo-4-p-tolylpiperidine-3-carboxylate

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; potassium acetate In 2,2,2-trifluoroethanol at 20℃; for 14h; optical yield given as %de; enantioselective reaction;

2-carboethoxy-N-methyl-acetamide (71510-95-7) + p-fluorocinnamoyl-3,5-dimethyl-1H-pyrazole → (3S,4R)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione (188302-25-2)

Conditions	Yield
Stage #1: 2-carboethoxy-N-methyl-acetamide; p-fluorocinnamoyl-3,5-dimethyl-1H-pyrazole With C32H46N4O4; ytterbium(III) triflate In dichloromethane at 35℃; for 0.333333h; Stage #2: With triethylamine In dichloromethane at 30 - 50℃; Reagent/catalyst;	51 g

2-carboethoxy-N-methyl-acetamide (71510-95-7) + C14H14N2O (37612-74-1) → C15H17NO4 + (3R,4S)-3-ethoxycarbonyl-4-(4-phenyl)-N-methylpiperidine-2,6-dione

Conditions	Yield
With C31H44N4O4; triethylamine; ytterbium(III) triflate In 1,2-dichloro-ethane at 40℃; for 72h; Molecular sieve; Inert atmosphere; Overall yield = 87 %; stereoselective reaction;	A n/a B n/a

2-carboethoxy-N-methyl-acetamide (71510-95-7) + C14H13FN2O → (3R,4S)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione + (3S,4R)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione (188302-25-2) + C15H16FNO4

Conditions	Yield
With (2S,2'S)-1,1'-(propane-1,3-diyl)bis(N-(2,6-dimethylphenyl)pyrrolidine-2-carboxamide)-N,N'-dioxide; triethylamine; ytterbium(III) triflate In dichloromethane at 35℃; for 72h; Inert atmosphere; Overall yield = 10 %;	A n/a B n/a C n/a

2-carboethoxy-N-methyl-acetamide (71510-95-7) + C14H13FN2O → (3S,4R)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione (188302-25-2) + C15H16FNO4

Conditions	Yield
With C35H52N4O4; triethylamine; ytterbium(III) triflate In dichloromethane at 35℃; for 72h; Inert atmosphere; Overall yield = 9 %;	A n/a B n/a

2-carboethoxy-N-methyl-acetamide (71510-95-7) + C14H13FN2O → trans 3-ethoxycarbonyl-4-(4'-fluorophenyl)-N-methyl-piperidine-2,6-dione (202534-94-9)

Conditions	Yield
Stage #1: 2-carboethoxy-N-methyl-acetamide With potassium tert-butylate In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; Stage #2: C14H13FN2O In dichloromethane at 20℃; for 24h; Inert atmosphere;

2-carboethoxy-N-methyl-acetamide (71510-95-7) + 3,5-dimethyl-1-[3-(4-chlorophenyl)propanonyl]pyrazole → C15H16ClNO4 + (3R,4S)-3-ethoxycarbonyl-4-(4-chlorophenyl)-N-methylpiperidine-2,6-dione

Conditions	Yield
With C31H44N4O4; triethylamine; ytterbium(III) triflate In 1,2-dichloro-ethane at 40℃; for 72h; Molecular sieve; Inert atmosphere; Overall yield = 92 %; stereoselective reaction;	A n/a B n/a

methyl-propanedioic acid (516-05-2) + 2-carboethoxy-N-methyl-acetamide (71510-95-7) → ethyl 1,5-dimethyl-2,4,6-pyridin-3-carboxylate

Conditions	Yield
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide; toluene at 20 - 35℃; for 56h; Temperature;

Upstream product

• 36239-09-5 ethyl chlorocarbonylacetate 
• 74-89-5 methylamine 
• 19172-47-5 Lawessons reagent 
• 156025-63-7 N-hydroxy-N-methyl-2-carbetoxyethanamide 
• 593-51-1 methylamine hydrochloride 
• 105-53-3 diethyl malonate 

Downstream Products

• 323203-12-9 C₁₅H₁₉NO₄ 
• 188302-25-2 (3S,4R)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione 

Relevant academic research and scientific papers

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