Granted Patent B2

US 8,759,589 · App. 13/248,696 · Granted Jun 24, 2014

Abstract

Claims (19)

1. A method for making 2-methoxymethyl-1,4-benzenediamine comprising hydrogenating 1-benzylamino-2-(methoxymethyl)-4-nitrobenzene in the presence of a hydrogenation catalyst.

2. The method of claim 1 , wherein the hydrogenation catalyst is palladium or platinum based.

3. The method of claim 1 , wherein the hydrogenating occurs in a hydrogenation solvent selected from a group comprising ethyl acetate, toluene, butyl acetate, ethanol and methanol.

4. The method of claim 1 , wherein the 1-benzylamino-2-(methoxymethyl)-4-nitrobenzene is obtained by introducing benzylamine to 4-nitro-2-methoxymethyl-chlorobenzene.

5. The method of claim 4 , wherein the introduction of benzylamine occurs in the presence of a phase transfer catalyst.

6. The method of claim 5 , wherein the phase transfer catalyst is tetraethylammonium bromide.

7. The method of claim 4 , wherein the 4-nitro-2-methoxymethyl-chlorobenzene is obtained by introducing a methoxymethyl group to 4-nitro-2-chloromethyl-chlorobenzene.

8. The method of claim 7 , wherein the introduction of the methoxymethyl group occurs by nucleophilic displacement.

9. The method of claim 7 , wherein the 4-nitro-2-chloromethyl-chlorobenzene is obtained by nitrating 2-chlorobenzylchloride.

10. A method of making 2-methoxymethyl-1,4-benzenediamine from 2-chlorobenzylchloride comprising:

a) nitrating the 2-chlorobenzylchloride to obtain 4-nitro-2-chloromethyl-chlorobenzene;

b) introducing a methoxymethyl group to the 4-nitro-2-chloromethyl-chlorobenzene to obtain 4-nitro-2-methoxymethyl-chlorobenzene;

c) introducing a benzylamine group to the 4-nitro-2-methoxymethyl-chlorobenzene to obtain 1-benzylamino-2-(methoxymethyl)-4-nitrobenzene; and

d) hydrogenating the 1-benzylamino-2-(methoxymethyl)-4-nitrobenzene in the presence of a hydrogenation catalyst to obtain the 2-methoxymethyl-1,4-benzenediamine.

11. The method of claim 10 , wherein the hydrogenation catalyst is palladium or platinum based.

12. The method of claim 10 , wherein the hydrogenating occurs in a hydrogenation solvent selected from a group comprising ethyl acetate, toluene, butyl acetate, ethanol and methanol.

13. The method of claim 10 , wherein the introducing of benzylamine occurs in the presence of a phase transfer catalyst.

14. The method of claim 13 , wherein the phase transfer catalyst is tetraethylammonium bromide.

15. The method of claim 10 , wherein the introducing of the methoxymethyl group to the 4-nitro-2-chloromethyl-chlorobenzene occurs by nucleophilic displacement.

Assignments (7)