Preparation of riboflavin

Details Preparation of riboflavin Preparation of riboflavin

1985-02-20

1987-06-16

Daus, Donald G.

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

534858, C07D48702

Patent

active

046737421

ABSTRACT:
Riboflavin of the formula I ##STR1## is prepared by condensation of a 4,5-dimethyl-N-(D)-ribityl-2-phenylazoaniline of the formula II ##STR2## where X is H, --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 acidic condensing agent in an inert organic solvent by an improved process in which the reaction is carried out in an aliphatic diol or triol derivative of the general formula IV ##STR4## where R.sup.1 is H or CH.sub.3, R.sup.2 is H or CH.sub.3 -- or, when n is 0, is CH.sub.3 --CO--O--CH.sub.2 --, R.sup.3 is CH.sub.3 --, C.sub.2 H.sub.5 -- or CH.sub.3 --, R.sup.4 is CH.sub.3 --CO--, or is H when R.sup.3 is CH.sub.3 -- or C.sub.2 H.sub.5 --, and n is 0 or 2, preferably 0, having a boiling point of 80.degree.-180.degree. C., or in a mixture of these as a solvent. In this process, the riboflavin is obtained in particularly pure form and in very good yields.

REFERENCES:
patent: 2343254 (1944-03-01), Dale
patent: 2847413 (1958-08-01), Folkers et al.
patent: 4567261 (1986-01-01), Ernst et al.
patent: 4567262 (1986-01-01), Grimmer et al.
Palzelt, et al., Chemical Abstracts, vol. 72, 111780k (1970).
Tishler, et al., J. Am. Chem. Soc., vol. 69, pp. 1487-1492, (1947).
Patzelt, et al., Chemical Abstracts, vol. 70, 68699k (1969) (abstract of Czech. 127,303, 04/15/68).
Gabriel, et al., Chemical Abstracts, vol. 98, 4749x (1983) (abstract of Czech. 195,229, 05/15/82).

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