Preparation of riboflavin

Details Preparation of riboflavin Preparation of riboflavin

1984-01-13

1986-01-28

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C07D47514

Patent

active

045672610

ABSTRACT:
Riboflavin of the formula I ##STR1## is prepared by condensing a 4,5-dimethyl-N-(D)-ribityl-2-phenylazoaniline of the formula II ##STR2## where R is H or --Cl, --NO.sub.2 or --CH.sub.3 in the o- or p-position, with barbituric acid of the formula III ##STR3## in the presence of an acid as the condensing agent, by an improved process in which the acidic condensing agent used is an aliphatic or cycloaliphatic/aliphatic tertiary carboxylic acid of the general formula IV ##STR4## where R.sup.1, R.sup.2 and R.sup.3 are each a lower alkyl group, R.sup.1, R.sup.2 and R.sup.3 together containing 3 to 20, preferably 3 to 10, carbon atoms, or R.sup.1 is a lower alkyl group, in particular methyl, and R.sup.2 and R.sup.3 together form a tetramethylene or pentamethylene group.
The process can be particularly advantageously carried out using trimethylacetic acid or a commercial mixture of saturated tertiary carboxylic acids, e.g. Versatic .sup.R 10-acid.

REFERENCES:
patent: 2155555 (1939-04-01), Karrer
patent: 2807611 (1957-09-01), Howe
patent: 2847413 (1958-08-01), Folkers et al.
Fatty Acids and Their Industrial Applications, ed. Pattison, Marcel Dekker, Inc., New York, (1968), pp. 366-368.
Berezouskii, et al., Chemical Abstracts, vol. 57, 1962, 11290i-11291a.
Tishler, et al., J. Am. Chem. Soc., 69, (1947), pp. 1487-1492.
Berezouskii, et al., J. Am. Chem. Soc., USSR 1961, pp. 3444-3448.
Haley, et al., J. Am. Chem. Soc., 76, (1954), pp. 2926-2929.

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