Org. Synth. 1932, 12, 58
DOI: 10.15227/orgsyn.012.0058
NITROBARBITURIC ACID
[Barbituric acid, 5-nitro-]
Submitted by W. W. Hartman and O. E. Sheppard.
Checked by C. S. Marvel and B. H. Wojcik.
1. Procedure
In a
2-l. flask, equipped with a
mechanical stirrer and surrounded by an
ice bath, is placed
143 cc. of fuming nitric acid (sp. gr. 1.52). Stirring is started, and
100 g. (0.61 mole) of barbituric acid (p. 60) is added over a period of two hours; the temperature is kept below 40° during the addition. The mixture is stirred for one hour after the
barbituric acid has been added, and stirring is continued while 430 cc. of water is added and the solution is cooled to 10°. The mixture is filtered, and the residue is washed with cold water and dried on a
glass tray at 60–80°
(Note 1). The
nitrobarbituric acid is dissolved by adding it to 860 cc. of boiling water in a 2-l. flask and heating the mixture on a boiling
water bath while steam is blown in until solution is complete
(Note 2). After filtration and cooling overnight, the crystals are removed, washed with cold water, and dried in trays in an
oven at 90–95° for two to three hours. The product melts with decomposition at
181–183° when heated rapidly. The yield is
139–141 g. (Note 3). On drying the product at 110–115° for two to three hours, the yield is
90–94 g. (
85–90 per cent of the theoretical amount) of an anhydrous compound which melts with decomposition at
176°.
2. Notes
1.
Unless the product is dried before recrystallization it is difficult to remove all the
nitric acid, and the final product will have a strong odor of
nitric acid.
2.
If a clear yellow solution is not obtained, Norite should be added before filtering.
3.
This yield is slightly above the theoretical yield of
139 g., but this is probably due to a greater degree of hydration than is indicated in the formula.
3. Discussion
Nitrobarbituric acid has been prepared by oxidation of
violuric acid,
1 and by treatment of
barbituric acid with fuming
nitric acid2 or concentrated
nitric acid.
3
This preparation is referenced from:
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
nitric acid (7697-37-2)
Barbituric acid (67-52-7)
Nitrobarbituric acid,
Barbituric acid, 5-nitro- (480-68-2)
violuric acid (87-39-8)
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