Preparation of 4-amino-1-naphthol ethers
View Patent ↗The present invention describes a process for preparing 4-amino-1-naphthol ethers which is characterized in that naphthol ethers are first prepared from 1-naphthols, the former are then converted to the corresponding 4-acetamino-1-naphthol ethers and then the acyl group is cleaved off, and further describes 4-acetamino-1-naphthol ethers obtained thereby.
1. 4-Acylamino-1-naphthol ethers of the general formula (VIIa)
where
R 1 is C 3 -C 12 -alkyl, C 2 -C 8 -haloalkyl, C 7 -C 13 -arylalkyl or substituents of the general formula (IV)
A-B (IV)
where
A is C 2 -C 8 -alkylene, C 2 -C 8 -haloalkylene and
B is NR 6 R 7 , SR 6 or OR 6
where
R 6 and R 7 are each independently substituted or unsubstituted C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 7 -C 12 -arylalkyl or C 6 -C 10 -aryl or
NR 6 R 7 together is a 5- to 8-membered heterocycle and
R 2 is hydrogen, halogen or C 1 -C 4 -alkyl and
R 3 is hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy and
n is zero, one, two, three or four and
R 4 are each independently halogen, nitro, cyano, protected formyl, C 1 -C 8 -alkyl, C 7 -C 10 -arylalkyl, C 1 -C 8 -hydroxyalkyl, C 1 -C 8 -haloalkyl or C 6 -C 10 -aryl or substituents of the general formula (II)
D-E-F (II)
where, independently,
D is absent or is a C 1 -C 8 -alkylene radical and
E is a carbonyl group or sulphonyl group and
F is R 6 , OR 6 , NH 2 , SR 6 , NHR 6 or NR 6 R 7
and where
R 6 and R 7 are each independently substituted or unsubstituted C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 7 -C 12 -arylalkyl or C 6 -C 10 -aryl or
NR 6 R 7 together is a 5- to 8-membered heterocycle and
R 5 is C 1 -C 6 -alkyl or C 1 -C 4 -haloalkyl.
2. 4-(2-([1]-naphthyloxy-[4]-acetamino)ethyl)morpholine.
3. 4-(2-([1]-naphthyloxy-[4]-propionylamino)ethyl)morpholine.
4. 4-(2-([1]-naphthyloxy-[4]-trifluoroacetamino)ethyl)morpholine.
5. Compounds of the general formula (VIIb)
where
R 5 is a C 1 -C 6 -alkyl or C 1 -C 4 -haloalkyl radical
and An−
is the anion of an acid.