Acetic nitro-, ethyl ester

PROPENOIC ACID, 3-NITRO-, ETHYL ESTER, (E)- [5941-50-4], 56,65 2-PROPEN-l-OL, 55,1 2-BROMO-3,3-DIPHENYL-, ACETATE [14310-15-71,56, 32... 

C4H7NO4 2-nitro-acetic acid ethyl ester 626-35-7... 

Archer, owing to very unfortunate coincidences, had mistaken acid potassium tartrate for the acetylamino acid. Goldfarb et al. prepared authentic 5-acetylamino-2-thiophenecarboxylic acid, mp 230 232°C (methyl ester, mp 171-171.5°C ethyl ester, mp 161°C), through reduction of 5-nitro-2-thiophenecarboxylic acid with Raney nickel in acetic anhydride and proved the structure by Raney nickel desulfurization to 8-aminovaleric acid. They also confirmed that the acid mp 272-273°C (methyl ester, mp 135-136°C ethyl ester, mp 116-117°C) is 4-acetylamino-2-thiophenecar boxy lie acid as originally stated by Steinkopf and Miiller. The statement of Tirouflet and Chane that the acid obtained upon reduction and acetylation of 5-nitro-2-thiophenecarboxylic acid melts at 272°C must result from some mistake as they give the correct melting point for the methyl ester. 

This procedure for the synthesis of ethyl 3-nitroacrylate is essentially that of Stevens and Emmons.2 Four major changes have been introduced by the submitters rapid introduction of dinitrogen tetroxide no purification of the intermediate nitro iodo ester use of dry, finely powdered sodium acetate for elimination of hydroiodic acid and percolation of the final product through a mat of alumina. With these modifications, the preparation is reproducible and highly efficient (80-90% overall). 

Melphalan and the racemic analog have been prepared by two general routes (Scheme I). In Approach (A) the amino acid function is protected, and the nitrogen mustard moiety is prepared by conventional methods from aromatic nitro-derivatives. Thus, the ethyl ester of N-phthaloyl-phenylalanine was nitrated and reduced catalytically to amine I. Compound I was reacted with ethylene oxide to form the corresponding bis(2-hydroxyethyl)amino derivative II, which was then treated with phosphorus oxychloride or thionyl chloride. The blocking groups were removed by acidic hydrolysis. Melphalan was precipitated by addition of sodium acetate and was recrystallized from methanol. No racemization was detected [10,28—30]. The hydrochloride was obtained in pure form from the final hydrolysis mixture by partial neutralization to pH 0.5 [31]. Variants of this approach, used for the preparation of the racemic compound, followed the same route via the a-acylamino-a-p-aminobenzyl malonic ester III [10,28—30,32,33] or the hydantoin IV [12]. 

This ring closure takes place readily whenever the carbonyl and amino groups occur in the relative positions shown above. Reduction of o-nitro-phenylacetonitrile by stannous chloride produces indole rather than the corresponding amino aldehyde. The synthesis is most useful for the preparation of indole-2-carboxylic acid by reduction of o-nitrophenyl-pyruvic acid with ferrous sulfate and ammonia or with sodium hydrosulfite. The ethyl ester is obtained by a similar reduction with zinc and acetic acid or by catalytic hydrogenation of ethyl o-nitrophenyl-pyruvate over platinum oxide catalyst. ... 

Nitro compounds, ar. Nitrobenzene, m-Dinitrobenzene o-Nitrophenol N-Nitramines Oxonium fluoroborate Trialky loxonium salt Trialky loxonium fluoroborate Pyrylium fluoroborate Carboxylic acid esters HCOOC Hs, p-Nitro-phenyl formate Isopropenyl acetate Salicylic acid esters Ethyl cyanoacetate Chloroformic acid esters Ethyl chloroformate, ClCOOC Hg-i Methyl trichloroacetate Diethyl oxalate Ethyl malonate... 

Nitro compounds, ar. Nitrobenzene N-Nitramines Oxonium fluoroborate Trialkyloxonium salt Trialkyloxonium fluoroborate Carboxylic acid esters Isopropenyl acetate Chloroformic acid esters Ethyl chloroformate Methyl trichloroacetate... 

The structures of donor-acceptor complexes of iyn-benzoyl azide, its 2-methyl- and 2,6-dimethyl-substituted derivatives with BF3, AICI3, and SbCls, and the transition states of the rearrangement into isocyanates have been reported by computational methods. The reaction of donor-substituted alkenes with a-diazo-a-nitro ethyl acetate under Rh catalysis have been reported which show that the nitro group is inserted forming cyclic nitronates, whereas the ester moiety was not incorporated into the ring system (Scheme 198). ... 

Nitro compounds, or. Nitrobenzene Oxonium fluoroborate Trialkyloxonium salt Trialkyloxonium fluoroborate Carboxylic acid esters Isopropenyl acetate Chloroformic acid esters Ethyl chloroformate Methyl trichloroacetate Ethyl malonate Orthoformic acid esters. Ethyl orthoformate (CH C0)20,(C2H C0)20, (CF2C0)20 n-Octanoic anhydride Butyl hydroperoxide Cumene hydroperoxide Peroxides... 

Nitro-filter cloths are composed of cellulose nitrate, which is an ester of cellulose. Any chemical compound that will saponify the ester will destroy the cloth. Caustic soda or potash in strengths of 2% at 70° C or over alkali sulfides, polysulfides and sulfohydrates or mixtures of ethyl alcohol and ether, ethyl, amyl and butyl acetates, pyridine, ferrous sulfates, and other reducing agents are detrimental to the cloth. 

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