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Generated: January 19, 2018

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Title: Process for the preparation of 4-haloalkylnicotinonitriles
Abstract:4-Haloalkylnicotinonitriles having the formula (I) ##STR1## which are suitable as intermediates in the preparation of pesticides, are obtained by: (a) reacting a 3-amino-1-haloalkyl-2-propen-1-one
Inventor(s): Pazenok; Sergiy (Kelkheim, DE), Bastiaans; Henricus Maria Martinus (Usingen, DE)
Assignee: Aventis Cropscience GmbH (Frankfurt, DE)
Filing Date:Dec 13, 2001
Application Number:10/013,470
Claims:1. A process for the preparation of a compound having the formula (I): ##STR10##

wherein R.sup.F is (C.sub.1 -C.sub.4)-haloalkyl, said process comprising: (a) reacting a 3-amino-1-haloalkyl-2-propen-1-one having the formula (II):

2. A process as claimed in claim 1, wherein the compound of formula (II) is reacted with at least one compound selected from the group consisting of a compound of the formula (III) and a compound of the formula (IV) under reduced pressure.

3. A process as claimed in claim 1, wherein the ring closure reaction is carried out in a solvent.

4. A process as claimed in claim 2, wherein the ring closure reaction is carried out in a solvent.

5. A process as claimed in claim 3, wherein the solvent is an alcohol.

6. A process as claimed in claim 4, wherein the solvent is an alcohol.

7. A process as claimed in claim 5, wherein the ring closure reaction is further carried out in the presence of a base.

8. A process as claimed in claim 6, wherein the ring closure reaction is further carried out in the presence of a base.

9. A process as claimed in claim 7, wherein the ring closure is further carried out in the presence of a weak base and is followed by acidification to afford the corresponding compound of formula (I).

10. A process as claimed in claim 8, wherein the ring closure is further carried out in the presence of a weak base and is followed by acidification to afford the corresponding compound of formula (I).

11. A process as claimed in claim 1, carried out as a one-pot process without isolation of intermediates.

12. A process as claimed in claim 1, wherein R.sup.F is CH.sub.2 F, CFCl.sub.2, CF.sub.2 Cl, CF.sub.3 or C.sub.2 F.sub.5.

13. A process as claimed in claim 12, wherein R.sup.F is CF.sub.3.

14. A process as claimed in claim 1, wherein R.sup.1 is (C.sub.1 -C.sub.4)-alkyl.

15. A process as claimed in claim 14, wherein R.sup.1 is methyl or ethyl.

16. A process as claimed in claim 1, wherein Z is O or NR.sup.1.

17. A process as claimed in claim 16, wherein R.sup.1 is (C.sub.1 -C.sub.4)-alkyl.

18. A process as claimed in claim 17, wherein R.sup.1 is methyl or ethyl.

19. A process for the preparation of a compound having the formula ##STR11##

wherein R.sup.F is (C.sub.1 -C.sub.4)-haloalkyl, said process comprising: (a) reacting a 3-amino-1-haloalkyl-2-propen-1-one having the formula (II):

20. A process as claimed in claim 19, wherein the compound of formula (II) is reacted with at least one compound selected from the group consisting of a compound of the formula (III) and a compound of the formula (IV).

21. A process as claimed in claim 19, wherein the ring closure reaction is carried out in a solvent.

22. A process as claimed in claim 20, wherein the ring closure reaction is carried out in a solvent.

23. A process as claimed in claim 21, wherein the solvent is an alcohol.

24. A process as claimed in claim 22, wherein the solvent is an alcohol.

25. A process as claimed in claim 23, wherein the ring closure reaction is further carried out in the presence of a base.

26. A process as claimed in claim 24, wherein the ring closure reaction is further carried out in the presence of a base.

27. A process as claimed in claim 25, wherein the ring closure is further carried out in the presence of a weak base and is followed by acidification to afford the corresponding compound of formula (I).

28. A process as claimed in claim 26, wherein the ring closure is further carried out in the presence of a weak base and is followed by acidification to afford the corresponding compound of formula (I).

29. A process as claimed in claim 19, carried out as a one-pot process without isolation of intermediates.

30. A process as claimed in claim 19, wherein R.sup.F is CH.sub.2 F, CFCl.sub.2, CF.sub.2 Cl, CF.sub.3 or C.sub.2 F.sub.5.

31. A process as claimed in claim 30, wherein R.sup.F is CF.sub.3.

32. A process as claimed in claim 19, wherein R.sup.1 is (C.sub.1 -C.sub.4)-alkyl.

33. A process as claimed in claim 32, wherein R.sup.1 is methyl or ethyl.

34. A process as claimed in claim 19, wherein Z is O or NR.sup.1.

35. A process as claimed in claim 34, wherein R.sup.1 is (C.sub.1 -C.sub.4)-alkyl.

36. A process as claimed in claim 35, wherein R.sup.1 is methyl or ethyl.
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