SYNTHESIS OF 2-, AND 3-NITROBENZANTHRONE VIA DIRECT NITRATION OF BENZANTHRONE WITH NITRIC ACID/ACETIC ACID

2019 ◽  
Vol 71 (1) ◽  
Author(s):  
Kefa K. Onchoke ◽  
Jorge J. Ojeda
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride ◽  
Standard Sample ◽  
Major Product ◽  
Fragmentation Patterns

Abstract Three mono-nitrobenzanthrone isomers (1-, 2-, and 3-nitrobenzanthrone; 1-, 2-, and 3-NBA) were synthesized by reacting benzanthrone (BA) with nitric acid (HNO3) in acetic anhydride at ice-cold conditions. The major product, 2-nitrobenzanthrone (2-NBA), was confirmed using GC-MS via comparisons with a standard sample. On the basis of the elution profiles and fragmentation patterns two other isomers formed were assigned to 1-, and 3-nitrobenzanthrone (1-, and 3-NBA). The average percent yields of 1-, 2-, and 3-NBA were 0.3 ± 0.1%, 10.5 ± 2.6 %, and 6.4 ± 1.3 %, respectively.

STUDIES ON RDX AND RELATED COMPOUNDS: X. ANALYSIS FOR NITRIC ACID IN ACETIC ACID – ACETIC ANHYDRIDE MEDIA

1953 ◽  
Vol 31 (3) ◽  
pp. 214-215 ◽  
Author(s):  
R. A. Marcus ◽  
C. A. Winkler
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride ◽  
Analytical Method ◽  
Potassium Acetate ◽  
Standard Solution ◽  
Related Compounds

An analytical method has been developed for the estimation of nitric acid in acetic acid – acetic anhydride media, with a precision of 0.3%. The procedure involves the addition of a solution of potassium acetate in acetic acid to the sample. The excess is back-titrated conductometrically with a standard solution of nitric acid in acetic acid.

scholarly journals On the Reaction of 4-(2'-Furyl)pyrimidine with Nitric Acid in Acetic Anhydride-Acetic Acid.

1967 ◽  
Vol 21 ◽  
pp. 2296-2298 ◽  
Author(s):  
Salo Gronowitz ◽  
Anders Hallberg ◽  
J. Sandström ◽  
S. J. Cyvin ◽  
G. Hagen
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride

The Nitration of α- and β-Acylnaphthalenes

1995 ◽  
Vol 48 (12) ◽  
pp. 1969 ◽  
Author(s):  
SD Barker ◽  
K Wilson ◽  
RK Norris
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride ◽  
Nitro Compound ◽  
Nitro Compounds ◽  
The Other ◽  
Coupling Constant ◽  
Significant Extent ◽  
Nitro Derivatives ◽  
High Yields

The nitration of α- and β- acylnaphthalenes with copper(II) nitrate in acetic anhydride or nitric acid/acetic acid mixtures gives high yields of the corresponding mononitro compounds. The assignment of constitution to these products is made on the basis of extensive 1H n.m.r. chemicl shift and coupling constant data. In the case of α- acylnaphthalenes, with the notable exception of α- pivalonaphthone, nitration occurs in the α-positions of the unsubstituted ring to give mixtures of 5- and 8-nitro compounds. α- Pivalonaphthone gives appreciable amounts of the 4-nitro compound and also of the 8-nitro compound. This result indicates that the pivaloyl group does not shield the 8-position sterically to any significant extent and is effectively electronically neutral, unlike the other acyl substituents , in allowing attack at the α-position (position 4) of the acylated ring. This result is ascribable to the lack of coplanarity of the pivaloyl group with the naphthalene system. All of the β- acylnaphthalenes gave mixtures of 4-, 5- and 8-nitro derivatives in proportions that did not vary significantly with the nature of the acyl group.

Adduct Intermediates in the Side-chain Nitration of 1,4-Dimethylnaphthalene

1972 ◽  
Vol 50 (24) ◽  
pp. 3988-3992 ◽  
Author(s):  
Alfred Fischer ◽  
Alan Leslie Wilkinson
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride ◽  
Room Temperature ◽  
Methylene Chloride ◽  
Side Chain ◽  
Trans Isomers ◽  
Cis And Trans Isomers ◽  
Cis And Trans ◽  
Naphthyl Acetate

cis and trans isomers of 1,4-dimethyl-4-nitro-1,4-dihydro-1-naphthyl acetate (1) have been isolated from a mixture of 1,4-dimethylnaphthalene and nitric acid in acetic anhydride by quenching at −40°. At room temperature only 1-methyl-4-nitromethylnaphthalene (4) is obtained. The conversion of 1,4-dimethylnaphthalene to 4 and of the cis (1a) and trans (1b) adducts to 4, by nitric acid in acetic anhydride, has been followed by n.m.r. 1,4-Dimethyl-4-nitro-1,4-dihydro-1-naphthyl nitrate (5) appears to be the immediate product from nitration of 1,4-dimethylnaphthalene in acetic anhydride, methylene chloride, or nitromethane. In acetic anhydride 5 is converted into 1. Decomposition of 1 in acetic acid gives 1,4-dimethyl-2-naphthyl acetate and some 4. The formation of 4 in this reaction is suppressed by urea.

STUDIES OF RDX AND RELATED COMPOUNDS: III. THE REACTION TO FORM RDX FROM AMMONIUM NITRATE AND FORMALDEHYDE IN ACETIC ANHYDRIDE

1951 ◽  
Vol 29 (5) ◽  
pp. 377-381 ◽  
Author(s):  
A. Gillies ◽  
H. L. Williams ◽  
C. A. Winkler
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride ◽  
Ammonium Nitrate ◽  
Glacial Acetic Acid ◽  
Related Compounds

This reaction at 35°C. exhibits a behavior indicative of the presence of an intermediate in the reaction. Reaction of paraformaldehyde and ammonium nitrate in glacial acetic acid resulted in the isolation of hexamine dinitrate. Evidence is presented to indicate that formation of hexamine dinitrate, accompanied by the production of nitric acid, is responsible for the production of RDX in the acetic anhydride system.

THE ADDITION OF CARBOXYLIC ACIDS TO ACETYLENIC COMPOUNDS

1966 ◽  
Vol 44 (19) ◽  
pp. 2241-2244 ◽  
Author(s):  
J. DiPietro ◽  
W. J. Roberts
Keyword(s):  
Molecular Weight ◽  
Acetic Acid ◽  
Free Radical ◽  
Acetic Anhydride ◽  
Formic Acid ◽  
Propionic Acid ◽  
Major Product ◽  
Organic Peroxides ◽  
General Scope ◽  
Acetylenic Compounds

The free radical induced addition of acetic acid and its derivatives to olefins has been reported recently. As an extension of this reaction, the addition of acetic acid to acetylenic compounds was investigated.Adipic acid was found to be the major product of the reaction of excess acetic acid and acetylene at 110–120 °C under pressure in the presence of organic peroxides. A second oily acidic product with a molecular weight of about 300, not yet identified, was found to the extent of about 2 parts by weight to every 3 parts of adipic acid.Octen-3-oic acid and its anhydride were synthesized from hexyne-1 and excess acetic acid in the presence of organic peroxides. Acetic anhydride was substituted for acetic acid, with the net advantage that acetylene was more soluble in the solvent. The general scope of the reaction was expanded to include other transfer agents, such as acetone, formic acid, and propionic acid.

The reaction of trialkylamine with nitric acid in a mixture of acetic acid and acetic anhydride

Tetrahedron ◽  
1968 ◽  
Vol 24 (8) ◽  
pp. 3425-3435 ◽  
Author(s):  
Y. Ogata ◽  
Y. Sawaki ◽  
Y. Kuriyama
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride
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