Preparation of riboflavin

Details Preparation of riboflavin Preparation of riboflavin

1986-11-19

1989-02-21

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

048066435

ABSTRACT:
Riboflavin of the formula I ##STR1## is prepared by an improved process by condensing a 4,5-dimethyl-N-(D)-ribityl-2-phenylazoaniline of the formula II ##STR2## where R is H, --CL, --NO.sub.2, --CH.sub.3 or --OCH.sub.3 in the o- or p-position, with barbituric acid of the formula III ##STR3## in the presence of an acid as a condensing agent, by a process in which the acidic condensing agent used is an aliphatic secondary carboxylic acid of the general formula IV ##STR4## where R.sup.1 is methyl or ethyl and R.sup.2 is alkyl of 3 or 4 carbon atoms.

REFERENCES:
patent: 4567261 (1986-01-01), Ernst et al.
patent: 4656275 (1987-04-01), Ernst et al.
patent: 4673742 (1987-06-01), Grimmer et al.
J.A.C.S., vol. 69, (1947), pp. 731, 1487-1491; "Thirteenth Report of the Committee on Atomic Weights of the International Union of Chemistry", Baxter et al. and . . . New Synthesis of Riboflavin by Tishler et al. (Berezovskii et al.).
J. Gen. Chem. USSR, (1961), vol. 31, pp. 3444-3448, "Investigations in the Alloxazine and Isoalloxazine Series v. Catalysts for the Reaction of Secondary Aromatic Orthoaminoazo Compounds with Trihydroxypyrimidines".
J.A.C.S., vol. 76, (1954), pp. 2926-2929, 2537; "Synthesis of D-Riboflavin-2-C and its Metabolism by Lactobacillus casei", Haley et al and Boron-Nitrogen Systems . . . , Brown et al.
WPIL Data Base Reference (Cites U.S. Pat. No. 4,673,742 as listed above).

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