Certain substituted 2,6-diamino-4-methyl-nicotinitriles the corresponding nicotinamides and derivatives thereof

Abstract

2,3,6- AND PREFERABLY ALSO 4-SUBSTITUTED PYRIDINE DERIVATIVES BEARING THE RADICAL OF AMMONIA OR A PRIMARY AMINE IN THE 2- AND 6-POSITIONS. The compounds are eminently suitable as coupling components for the production of azo dyes, the coupling taking place in the 5-position.

We claim: 
     
       1. A compound of the formula ##STR211## in which: R 1  is hydrogen, alkyl of one to seven carbon atoms or phenyl; X is cyano or carbamoyl; and   each Z, independently of one another, is hydrogen, alkyl of one to eight carbon atoms, hydroxyalkyl of two to eight carbon atoms, cyanoalkyl of two to seven carbon atoms, alkoxyalkyl of two or three carbon atoms in the alkyl and one to eight carbon atoms in the alkoxy, cyclohexoxypropyl, benzyloxypropyl, β-phenyl-ethoxypropyl, phenoxypropyl, tolyloxypropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, hydroxycyclohexyl, β-hydroxyethoxycyclohexyl, norbornyl, hydroxynorbornyl, hydroxymethylnorbornyl, chloromethylnorbornyl, β-hydroxyethylnorbornyl, bicyclooctyl, phenylalkyl or tolylalkyl of one to four carbon atoms in the alkyl, phenyl, phenyl substituted by methyl, methoxy, ethoxy, hydroxy, chloro or β-hydroxyethoxy, allyl, carboxyethyl, carboxypentyl, ω-pyrrolidonylalkyl of two to six carbon atoms in the alkyl, ##STR212## --(CH 2 ) 2  O(CH 2 ) 2  OH, --(CH 2 ) 3  O(CH 2 ) 4  OH, --(CH 2 ) 3  O(CH 2 ) 6  OH, ##STR213## or --(CH 2 ) 3  (OC 2  H 4 ) n  OT, n being 1, 2, 3 or 4, and   T being hydrogen, alkyl of one to four carbon atoms, benzyl, phenylethyl, cyclohexyl, phenyl or tolyl.   
     
     
       2. A compound as claimed in claim 1 of the formula ##STR214## in which: Z 1  is an oxygen-containing radical selected from the group consisting of --CH 2  CH 2  OH, --CH 2  CH 2  Ch.sub. 2 OH, ##STR215## --(CH 2 ) 3  O(CH 2 ) 2  OH, --(CH 2 ) 3  O(CH 2 ) 4  OH, --(CH 2 ) 3  O(CH 2 ) 6  OH, --(CH 2 ) 4  OH, --(CH 2 ) 6  OH, --(CH 2 ) 2  O(CH 2 ) 2  OH, ##STR216## --CH 2  CH 2  OCH 3 , --CH 2  CH 2  OC 2  H 5 , --CH 2  CH 2  OC 4  H 9 , --(CH 2 ) 3  OCH 3 , --(CH 2 ) 3  OC 2  H 5 , --(CH 2 ) 3  OC 4  H 9 , --(CH 2 ) 3  OC 3  H 7 , --(CH 2 ) 3  OC 6  H 13 , --(CH 2 ) 3  OC 8  H 17 , ##STR217## --(CH 2 ) 3  OC 2  H 4  OCH 3 , --(CH 2 ) 3  OC 2  H 4  OC 4  H 9 , ##STR218## and --(CH 2 ) 3  OC 2  H 4  OC 6  H 5  ; and Z 2  is hydrogen, an oxygen-containing radical as defined for Z 1  or an oxygen-free radical selected from the group consisting of   --C 2  H 5 , --C 3  H 7 , --C 4  H 9 , ##STR219## --CH 2  C 6  H 5 , --C 2  H 4  C 6  H 5 , --C 3  H 7  C 6  H 5 , ##STR220## --C 6  H 5 , --C 6  H 4  CH 3  and --C 6  H 4  OCH 3 .   
     
     
       3. the compound of the formula ##STR221## 
     
     
       4. The compound of the formula ##STR222## 
     
     
       5. The compound of the formula ##STR223## 
     
     
       6. The compound of the formula ##STR224##