Carboxylic acid reaction with ammonia

Reaction with water to yield a carboxylic acid Reaction with an alcohol to yield an ester Reaction with ammonia or an amine to yield an amide Reaction with a hydride reducing agent to yield an aldehyde or an alcohol... 

TETRINE ACID (60-00-4) CioH.sNjOg A weak organic (carboxylic) acid. Reaction with dithiocarbamates, isocyanates, mercaptans, nitrides, nitrites, sulfides, forms flammable and/or toxic gases + heat. Incompatible with acids, azo compounds, epoxides and other polymerizable compounds oxidizers, sulfuric acid, reducing agents bases, ammonia, aliphatic amines alkanolamines, alkylene oxides cyanide salts and cyanide solutions (forms... 

Amidation, the formation of amides. Amino acid and peptide amides are synthesized by reaction of the appropriate esters or activated carboxylic acid derivatives with ammonia. Amidation of bioactive peptides is performed using the bifunctional enzyme peptidylglycine a-amidating monooxygenase (PAM) by N-oxidative cleavage of a glycine-extended precursor [S. T. Prigge et al.. Science 1997, 278, 1300]. 

An amide is produced in a reaction called amidation, in which a carboxylic acid reacts with ammonia or an amine. A molecule of water is eliminated, and the fragments of the carboxylic acid and amine molecules join to form the amide, much like the formation of... 

Some of the physical properties of fatty acid nitriles are Hsted in Table 14 (see also Carboxylic acids). Eatty acid nitriles are produced as intermediates for a large variety of amines and amides. Estimated U.S. production capacity (1980) was >140, 000 t/yr. Eatty acid nitriles are produced from the corresponding acids by a catalytic reaction with ammonia in the Hquid phase. They have Httie use other than as intermediates but could have some utility as surfactants (qv), mst inhibitors, and plastici2ers (qv). 

The carboxyl groups of amino acids undergo all the simple reactions common to this functional group. Reaction with ammonia and primary amines yields unsubstituted and substituted amides, respectively (Figure 4.9a,b). Esters... 

The ketocarbene 4 that is generated by loss of Na from the a-diazo ketone, and that has an electron-sextet, rearranges to the more stable ketene 2 by a nucleophilic 1,2-shift of substituent R. The ketene thus formed corresponds to the isocyanate product of the related Curtius reaction. The ketene can further react with nucleophilic agents, that add to the C=0-double bond. For example by reaction with water a carboxylic acid 3 is formed, while from reaction with an alcohol R -OH an ester 5 is obtained directly. The reaction with ammonia or an amine R -NHa leads to formation of a carboxylic amide 6 or 7 ... 

When the -OH of a carboxylic acid is replaced by an -NH2, the compound produced is an amide. Amides are neutral to mildly basic compounds. They can be made from acids, acid chlorides, acid anhydrides, and esters by reaction with ammonia or primary and secondary amines. The amide linkage is found in polyamide resins such as nylon. 

Other Gas Reactions. Several other reactive gases or vapours were examined but found to be unsatisfactory. No ester formation ( 1745 cm"1) was found when oxidatized films were exposed to acetic acid or formic acid vapour. Alcohol/carboxylic acid reactions in the solid state have often been suggested as the source of ester products, but not substantiated (4,5). Gaseous ammonia reacted with carboxylic acid groups to give absorptions at 1550 cm"1 [-C(=0)-0 ] and 1300 cm"1 (NHi +). However, these absorptions were very broad and the method inferior to acid measurement by SF. Although N20 did not react with oxidized polyolefins, the reaction of N02 with oxi-... 

Electrophilic substitution of the ring hydrogen atom in 1,3,4-oxadiazoles is uncommon. In contrast, several reactions of electrophiles with C-linked substituents of 1,3,4-oxadiazole have been reported. 2,5-Diaryl-l,3,4-oxadiazoles are bromi-nated and nitrated on aryl substituents. Oxidation of 2,5-ditolyl-l,3,4-oxadiazole afforded the corresponding dialdehydes or dicarboxylic acids. 2-Methyl-5-phenyl-l,3,4-oxadiazole treated with butyllithium and then with isoamyl nitrite yielded the oxime of 5-phenyl-l,3,4-oxadiazol-2-carbaldehyde. 2-Chloromethyl-5-phenyl-l,3,4-oxadiazole under the action of sulfur and methyl iodide followed by amines affords the respective thioamides. 2-Chloromethyl-5-methyl-l,3,4-oxadia-zole and triethyl phosphite gave a product, which underwent a Wittig reation with aromatic aldehydes to form alkenes. Alkyl l,3,4-oxadiazole-2-carboxylates undergo typical reactions with ammonia, amines, and hydrazines to afford amides or hydrazides. It has been shown that 5-amino-l,3,4-oxadiazole-2-carboxylic acids and their esters decarboxylate. 

Acid chlorides are very reactive, and they readily react with ammonia, primary amines, or secondary amines to form an amide. Figure 12-26 illustrates the reaction of an acid chloride with ammonia. Replacing one or two of the hydrogen atoms of ammonia with an organic group will result in an N-substituted amide. Tertiary amines react with acid chlorides to form a carboxylic acid and an ammonium salt. 

Reaction of the imidazole (7-4) with the benzofuran derivative (6-7) leads to the displacement of the benzylic halogen and the formation of the alkylation product (8-1). Treatment of that intermediate with trifluoroacetic acid breaks open the urethane to afford the corresponding free amine. This is allowed to react with ttiflic anhydride to afford the trifluoromethyl sulfonamide (8-2). The ester group on the imdidazole is then saponified, and the newly formed acid is reacted with carbonyl diimidazole. Reaction with ammonia converts the activated carboxyl group to the amide. There is thus obtained the angiotensin antagonist saprisartan (8-3) [6]. 

Treatment of ethyl l-oxo-l//-pyrimido[l,2-a]quinoline-2-carboxylates with ammonia in methanol and hydrazine hydrate in ethanol at ambient temperature afforded 2-carboxamides and 2-carbohydrazides, respectively (74MIP1 79MIP2). Reaction of l-oxo-l//-pyrimido[l,2,-a]quinoline-2-carboxylic acids (169) with A-. /V-carbonyldiimidazole in dimethyl-formamide, then with 5-aminotetrazole gave 7V-(5-tetrazolyl)-1 -oxo-1H-pyrimido[l,2-a]quinoline-2-carboxamides (170) (77GEP2630469 77USP 4017625). 

Fatty acid nitriles are produced as intermediates for a large variety of amines and amides. See also Carboxylic Acids. Fatty acid nitriles are produced from the corresponding acids by a catalytic reaction with ammonia in the liquid phase. They have little use other than as intermediates. 

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