Method for preparing 2-phenylbenzotriazoles and 2-phenylbenzotri

Details Method for preparing 2-phenylbenzotriazoles and 2-phenylbenzotri Method for preparing 2-phenylbenzotriazoles and 2-phenylbenzotri

1986-09-11

1988-10-25

Daus, Donald G.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548257, 548261, C07D24920

Patent

active

047805412

ABSTRACT:
This invention relates to a method for preparing a 2-phenylbenzotriazole of formula I, ##STR1## (wherein R.sub.1 represents hydrogen or chlorine atom, a lower alkyl group having a carbon number of 1 to 4, a lower alkoxyl group having a carbon number of 1 to 4, carboxyl group, or sulfonic acid group; R.sub.2 represents hydrogen or chlorine atom, a lower alkyl group having a carbon number of 1 to 4, or a lower alkoxyl group having a carbon number of 1 to 4; R.sub.3 represents hydrogen or chlorine atom, an alkyl group having a carbon number of 1 to 12, a lower alkoxyl group having a carbon number of 1 to 4, phenyl group, a phenyl group substituted with an alkyl group having a carbon number of 1 to 8, phenoxy group, or a phenylalkyl group, the alkyl part of which has a carbon number of 1 to 4; R.sub.4 represents hydrogen or chlorine atom, hydroxyl group, or a lower alkoxyl group having a carbon number of 1 to 4; and R.sub.5 represents hydrogen atom, an alkyl group having a carbon number of 1 to 12, or a phenylalkyl group, the alkyl part of which has a carbon number of 1 to 4), which comprises reducing an o-nitroazobenzene of formula III, ##STR2## (wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined above) with an aldehyde reducing agent in the presence of an aromatic ketone catalyst and base.
This invention further relates to a method for preparing a 2-phenylbenzotriazole of formula I as derfined above, which comprises reducing 1 mole 2-phenylbenzotriazole-N-oxide of formula II, ##STR3## (wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined above) with 1 to 4 mole aldehyde in the presence of an aromatic ketone catalyst and base.
This invention still further relates to a method for preparing a 2-phenylbenzotriazole-N-oxide of formula II as defined above, which comprises reducing 1 mole o-nitroazobenzene of formula III as defined above with 1 to 2 mole aldehyde in the presence of an aromatic ketone catalyst and base.

REFERENCES:
patent: 4642350 (1987-02-01), Davatz
Fieser and Fieser, Organic Chemistry, 3rd Ed. (1956: Reinhold Publishing Co., New York), pp. 350 and 362.
March, J., Advanced Organic Chemistry, 2nd Ed. (1977: McGRaw-Hill Book Co., New York), p. 1138.

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