Determination of Nitrogen in Difficultly Combustible Ring Compounds

Brancone, L. M.; Fulmor, W.

doi:10.1021/ac60033a040

Cited by 17 publications

(6 citation statements)

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“…Satisfactory results were obtained by adding a small amount of silver oxide to the combustion tube when a sample was charged. 16 (15) A. Albert, Quart. Rev.…”

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confidence: 99%

Synthesis of an isomer of pteroic acid, 4-[(2-amino-4-hydroxyprimido[5,4-d]pyrimidin-6-ylmethyl)amino]benzoic acid

Kim¹,

McKee²

1970

J. Org. Chem.

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4-[(2-Amino-4-hydroxypyrimido [5,4-d] pyrimidin-6-ylmethyl)amino] benzoic acid (3) and its 2-hydroxy analog (4), in which C7 and Ns of the pteridine nucleus are interchanged, were synthesized in seven steps from 5-bromo-2-hydroxymethyl-4-pyrimidinecarboxylic acid. Efforts to condense p-carbethoxyanilinoacetamidine hydrochloride (6) with mucobromic acid did not succeed.Many chemically modified analogs of pteroylglutamic acid (2) and pteroic acid (1) are known to antagonize the growth-promoting activity of the vitamin 2 which is known to function in its tetrahydro form.3Recent interest in this field has been centered on the preparation and biochemical study of deazapteridine analogs in efforts to determine the structural requirements for the biological activity.4 No attempt has heretofore been made, however, to investigate the effect on the activity of changing the relative positions of the nitrogen atoms in the pteridine nucleus.We have been particularly interested in an isomer in which C7 and Ns of the pteridine ring of pteroic acid are interchanged. This paper describes the synthesis of 3, in which this interchange has been accomplished.An initial approach to this synthesis involved the preparation of 2-amino-6-methylpyrimido [5,4-d]pyrimidin-4-ol and unsuccessful efforts to attach p-aminobenzoic acid at the 6-methyl site.5 It seemed more promising, therefore, to prepare first a pyrimidine ring with the desired side chain followed by construction of the second pyrimidine ring. Accordingly, condensation of p-carbethoxyanilinoacetamidine hydrochloride (6) with mucobromic acid was attempted. Then the (1) (a) This investigation was supported by Public Health Service Research Grant CA-05781 from the National Cancer Institute, for which a grateful acknowledgment is expressed, (b) Abstracted in part from a thesis submitted by D. . K. to the University of North Carolina in partial fulfillment of requirements for the Ph.D. degree, 1965.

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“…Satisfactory results were obtained by adding a small amount of silver oxide to the combustion tube when a sample was charged. 16 (15) A. Albert, Quart. Rev.…”

mentioning

confidence: 99%

Synthesis of an isomer of pteroic acid, 4-[(2-amino-4-hydroxyprimido[5,4-d]pyrimidin-6-ylmethyl)amino]benzoic acid

Kim¹,

McKee²

1970

J. Org. Chem.

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“…Several attempts have been made to overcome this difficulty. Hayman and Adler (4) achieved some success by adding powdered copper acetate to the temporary filling to catalyze combustion, but others (1,12,13) found the method unsatisfactory. Spies and Harris (13) and Ronzio (12) suggested the use of potassium chlorate, or other strong oxidants, to promote complete combustion of the by hot copper, and the nitrogen is swept into potassium hydroxide with carbon dioxide.…”

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confidence: 99%

Microdetermination of Nitrogen in Organic Compounds

Alford¹

1952

Anal. Chem.

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VOLUME 2 4, NO. 5, MAY 1952 881 7 years without significant changes. An analysis of a sample in duplicate requires 40 minutes, including the time required to weigh the samples and the mass spectrometric analysis.The authors have successfully analyzed with this apparatus the following types of compounds: fatty acids, amino acids, sugars, porphyrins, sterols, halogen, nitro and thio compounds, and salts of organic acids. In the analysis of sulfur-containing compounds care must be exercised that the oxides of sulfur do not reach trap C.

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“…The sign " + " means a positive color reaction and the sign Compounds Containing Neither Methyl Ketone nor Methyl Carbinol Groups, but Showing Positive Iodoform Reactions. Styraxinolic acid (5) (B + , C + ), acetyl styraxinic acid (5) (B + , C -), , -dibenzoylethane (7) (B+, C + ), cholesterol (1) (B+, C -), dibenzalacetone (J) (B + , C + ), -phenyl-[/3methvl, phenylj-ethvleneglvcol (1) (B + , C + ), citric acid (7) (B -, C -).…”

mentioning

confidence: 99%

Determination of Nitrogen by Micro-Dumas Procedure

Shelberg¹

1951

Anal. Chem.

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Determination of Nitrogen in Difficultly Combustible Ring Compounds

Cited by 17 publications

References 1 publication

Synthesis of an isomer of pteroic acid, 4-[(2-amino-4-hydroxyprimido[5,4-d]pyrimidin-6-ylmethyl)amino]benzoic acid

Synthesis of an isomer of pteroic acid, 4-[(2-amino-4-hydroxyprimido[5,4-d]pyrimidin-6-ylmethyl)amino]benzoic acid

Microdetermination of Nitrogen in Organic Compounds

Determination of Nitrogen by Micro-Dumas Procedure

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