Method for preparing 2-lower alkyl-substituted naphthoxazoles by

Details Method for preparing 2-lower alkyl-substituted naphthoxazoles by Method for preparing 2-lower alkyl-substituted naphthoxazoles by

1980-10-02

1984-07-17

Daus, Donald G.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

568735, C07D49800, C07D26360

Patent

active

044607792

ABSTRACT:
The invention relates to a method for preparing 2-lower alkyl-substituted naphthoxazoles by way of non-toxic intermediates, and in particular relates to the preparation of a 2-lower alkyl-naphtho-[2,1-d]-oxazole or a 2-lower alkyl-naphtho-[1,2-d]-oxazole, which are of industrial interest in the field of cyanine dyes for use in photography, and in the field of optical brighteners for use in plastic materials. According to the invention, an aldehyde of a lower alkyl is reacted with 2-nitroso-1-naphthol or with 1-nitroso-2-naphthol, in the presence of a strong acid and a non-aqueous organic solvent, and the condensation product is then reduced.

REFERENCES:
patent: 3653943 (1972-04-01), Kaempfen
Allan, A. W., et al., J. Chem. Soc. (c), 1397-1399, (1968).
Katritzky et al., "Advances in Heterocyclic Chemistry," vol. 17, pp. 130-131, (1974).
Selwitz, C. M., et al., J. Amer. Chem. soc., 77. pp. 5370-5373, (1955).
Elderfield, "Heterocyclic Compounds", vol. 5, pp. 314-317, John Wiley & Sons, Inc. New York.
Stein, C. W. C., et al., J. Amer. Chem. Soc., 64, pp. 2567-2569, (1942).
Morrison and Boyd, "Organic Chemistry," p. 1005, 3rd Ed. Allyn and Bacon, Inc., Boston, (1974).
Osman & Bassiuni, Journal of Organic Chemistry, vol. 27, (1962), 558.
Buehler & Pearson, Survey of Organic Synthesis, p. 417.

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