- A Convenient and greener Synthesis of Methyl Nitroacetate
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A new procedure for the synthesis and isolation of methyl nitroacetate is described. The previously published method required drying the explosive dipotassium salt of nitroacetic acid in a vacuum desiccator, followed by grinding this material into a fine powder with a mortar and pestle prior to esterification. To obtain the desired product, benzene was employed as the extraction solvent, sodium sulfate was used as the drying agent, and two distillations were required. The new procedure eliminates drying and grinding of the explosive dipotassium salt, employs ethyl acetate or dichloromethane as the extraction solvent, eliminates the need for a drying agent, and requires a single distillation to furnish the end product in high yield and purity.
- Johnson, Eric C.,Guzmán, Pablo E.,Wingard, Leah A.,Sabatini, Jesse J.,Pesce-Rodriguez, Rose A.
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- Direct one-pot synthesis of 3-nitroquinolin-2(1H)-one via H2O/AcOH system: An improvement to classical Friedlander reaction
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Quinolin-2(1H)-ones and their derivatives have attracted considerable attention because of their extensive applications in the field of pharmaceuticals, agricultural and dye chemistry. In contrast to the existed synthetic methods, herein we present the one-pot cascade reaction of 1,1-dimeoxyth-2-nitroethene and 2-aminobenzaldehydes which is catalyst-free and via eco-friendly H2O/AcOH solvent, achieving 3-nitroquinolin-2(1H)-ones in moderate to excellent yields. Importantly, this concise and versatile protocol is a potential improvement to the traditional Friedlander reaction.
- Chen, Xin-fei,Ren, Chao,Xu, Xiao-yong,Shao, Xu-sheng,Li, Zhong
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p. 1433 - 1436
(2017/03/23)
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- First chemoenzymatic synthesis of (+)-2-carboxypyrrolidine-3-acetic acid, the nucleus of kainoid amino acids
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The distinctive nucleus of kainoid amino acids, (2S,3R)-(+)-2- carboxypyrrolidine- 3-acetic acid 6, was synthesized by a chemoenzymatic process, exploiting the diastereomeric cis/ trans methyl pyroglutamate derivatives 10a-c/11a-c as key intermediates. These mixtures, when subjected to a kinetic resolution mediated by α-chymotrypsin, reacted diastereo-, regio-, and enantioselectively to give the trans derivatives (+)-10a-c possessing the correct (2S,3R) configuration. Subsequently, the desired product (2S,3R)-(+)-6 could be obtained after well-established transformations.
- Felluga, Fulvia,Forzato, Cristina,Nitti, Patrizia,Pitacco, Giuliana,Ghelfi, Franco,Valentin, Ennio
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experimental part
p. 112 - 118
(2012/02/16)
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- Synthesis of α-functional nitro compounds by the nitration of activated carbonyl compounds in a two-phase system
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2-Nitro-1,3-dicarbonyl and α-nitromonocarbonyl compounds were synthesized in the yields variyng from moderate (30percent) to nearly quantitative by the nitration of β-dicarbonyl compounds in a two-phase system: sulfuric/nitric acid mixture - chloroform at -10 - 10 deg C.The use of phase transfer conditions made it possible to avoid the formation of furoxans as by-products and to simplify the isolation of products.This method is quite common for preparing various α-functional nitro compounds including those containing a CF3-group. - Key words: nitration, α-functional nitro compounds.
- Kislyi, V. P.,Laikhter, A. L.,Ugrak, B. I.,Semenov, V. V.
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- Method for preparing an ester of nitroacetic acid
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There is disclosed a method for preparing an ester of nitroacetic acid which comprises; (1) a first step of subjecting a vinyl ester of a fatty acid and a nitrogen oxide to reaction with each other in the presence of a gas containing molecular oxygen in a solvent; and (2) a second step of subjecting the resultant reaction product of the first step to reaction with an alcohol. According to the method of this invention, an ester of nitroacetic acid can effectively be obtained in higher yield.
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- REACTION OF HALOGENO- AND DIHALOGENONITROACETIC ESTERS WITH TRIPHENYLPHOSPHINE
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The reaction of halogeno- and dihalogenonitroacetic esters with triphenylphosphine in mixtures with protic and aprotic solvents leads to the formation of triphenylphosphine oxide and to substitution of one halogen atom in the esters by a hydrogen atom.
- Martynov, I. V.,Postnova, L. V.,Bikkineev, R. Kh.,Yurtanov, A. I.
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p. 1571 - 1573
(2007/10/02)
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- Carboxylation of Nitromethane by Carbon Dioxide and Potassium Phenoxide Derivatives. Substituent Effect upon the Yield of Carboxylate
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The carboxylation of nitromethane with carbon dioxide proceeded in the presence of potassium phenoxides in DMF, yielding dipotassium nitoacetate as a precipitate.This reaction proceeded well at 0 deg C.The substituent effect upon the carboxylation was investigated by using potassium phenoxides with various substituents (p-OCH3, p-CH3, H, p-Cl, m-Cl, p-COCH3, and p-NO2).The reaction was completed in 5 min at 0 deg C.The maximum yield of carboxylate was obtained when unsubstituted phenoxide was used; the yield of carboxylate was low when potassium phenoxide with a substituent having a highly negative or highly positive ? value vas used.The mechanism of the carboxylation is discussed.The formation of the carboxylate as a precipitate is considered to be an important factor.Methods for the effective transformation of dipotassium nitroacetate to methyl nitroacetate are briefly surveyed.Keywords - potassium phenoxide; carbon dioxide; nitromethane; dipotassium nitroacetate; substituent effect; carboxylation
- Mori, Hisakazu,Okubo, Mutsuko,Oke, Yoshiko,Noguchi, Nobuko,Fukuda, Miho,Ishihara, Masao
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p. 2200 - 2204
(2007/10/02)
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- Esters of nitro(tetrahydro-2H-1,3-thiazin-2-ylidene)acetic acids
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Novel insecticidal esters of nitro(tetrahydro-2H-1,3-thiazin-2-ylidene)acetic acids.
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