Compound and process

1. A nitrile compound or a salt thereof, which nitrile compound is a compound of formula (A):

wherein:

R 1 and R 2 are the same or different and each is independently a C 1 -C 6 alkyl group or a C 2 -C 7 acyl group, or R 1 and R 2 together form a C 1 -C 6 alkylene group;

R 3 and R 4 are the same or different and each is independently hydrogen, halogen or a C 1 -C 6 alkyl group;

R 5 and R 6 are the same or different and each is independently hydrogen, halogen or a C 1 -C 6 alkyl group;

X is CHR 7 , O or NR 7 , and R 7 is hydrogen or a C 1 -C 6 alkyl group; and

Ar is a C 6 -C 10 aryl group substituted with from 0 to 4 substituents, each of which substituents is independently halogen or a C 1 -C 6 alkyl group.

2. A nitrile compound according to claim 1 or a salt thereof, wherein the nitrile compound is a compound of formula (D):

3. A process for producing a nitrile compound of formula (A) as defined in claim 1 , which process comprises reacting a compound of formula (I) with a compound of formula (II):

wherein

R 1 and R 2 are the same or different and each is independently a C 1 -C 6 alkyl group or a C 2 -C 7 acyl group, or R 1 and R 2 together form a C 1 -C 6 alkylene group;

R 3 and R 4 are the same or different and each is independently hydrogen, halogen or a C 1 -C 6 alkyl group;

R 5 and R 6 are the same or different and each is independently hydrogen, halogen or a C 1 -C 6 alkyl group;

X is CHR 7 , O or NR 7 , and R 7 is hydrogen or a C 1 -C 6 alkyl group;

Ar is a C 6 -C 10 aryl group substituted with from 0 to 4 substituents, each of which substituents is independently halogen or a C 1 -C 6 alkyl group; and

Y is a leaving group.

4. A process according to claim 3 , wherein:

R 1 and R 2 are methyl;

R 3 and R 4 are hydrogen;

R 5 and R 6 are hydrogen;

X is CH 2 ; and

Ar is 2,4,6-trimethylphenyl.

5. A process according to claim 3 , wherein Y is a leaving group which is Cl, Br, I, —OC(O)R Y , —OS(O) 2 R Y and —S(O) 2 R Y , where R Y is hydrogen, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group or a C 6 -C 10 aryl group, which alkyl, alkoxy or aryl group is optionally substituted with from 1 to 6 halide groups.

6. A process according to claim 3 , wherein the amount of the compound of formula (II) is from 0.5 to 10.0 equivalents of the compound of formula (I).

7. A process according to claim 3 , wherein the process comprises reacting the compound of formula (I) and the compound of formula (II) in the presence of a base.

8. A process according to claim 7 , wherein the base comprises carbonate, hydrogen carbonate, an alkoxide, a carboxylate or an amine.

9. A process according to claim 7 , wherein the amount of the base is from 1.0 to 10.0 equivalents of the compound of formula (I).

10. A process according to claim 3 , wherein the process comprises reacting the compound of formula (I) and the compound of formula (II) in the presence of a solvent.

11. A process according to claim 3 , wherein the process comprises reacting the compound of formula (I) and the compound of formula (II) for at least 5 hours.

12. A process according to claim 3 , wherein the process comprises reacting the compound of formula (I) and the compound of formula (II) at a temperature of from 50 to 100° C.

13. A process for producing a compound of formula (B):

which process comprises reducing a compound of formula (A) as defined in claim 1 .

14. A process according to claim 13 , wherein reducing the compound of formula (A) comprises hydrogenating the compound of formula (A) in the presence of nickel, Raney nickel, palladium, palladium black, palladium hydroxide, platinum and platinum dioxide.

15. A process according to claim 13 , which process further comprises producing the compound of formula (A) by a process comprising reacting a compound of formula (I) with a compound of formula (II):

wherein

R 1 and R 2 are the same or different and each is independently a C 1 -C 6 alkyl group or a C 2 -C 7 acyl group, or R 1 and R 2 together form a C 1 -C 6 alkylene group,

R 3 and R 4 are the same or different and each is independently hydrogen, halogen or a C 1 -C 6 alkyl group;

R 5 and R 6 are the same or different and each is independently hydrogen, halogen or a C 1 -C 6 alkyl group;

X is CHR 7 , O or NR 7 , and R 7 is hydrogen or a C 1 -C 6 alkyl group, and

Ar is a C 6 -C 10 aryl group substituted with from 0 to 4 substituents, each of which substituents is independently halogen or a C 1 -C 6 alkyl group, and

Y is a leaving group.

16. A process for producing a compound of formula (C):

wherein

R 1 and R 2 are the same or different and each is independently a C 1 -C 6 alkyl group or a C 2 -C 7 acyl group, or R 1 and R 2 together form a C 1 -C 6 alkylene group;

R 3 and R 4 are the same or different and each is independently hydrogen, halogen or a C 1 -C 6 alkyl group;

R 5 and R 6 are the same or different and each is independently hydrogen, halogen or a C 1 -C 6 alkyl group;

X is CHR 7 , O or NR 7 , and R 7 is hydrogen or a C 1 -C 6 alkyl group; and

Ar is a C 6 -C 10 aryl group substituted with from 0 to 4 substituents, each of which substituents is independently halogen or a C 1 -C 6 alkyl group; and

Q is O, NR 8 or CR 8 and R 8 is hydrogen or a C 1 -C 6 alkyl group,

which process comprises:

(i) a process for producing a compound of formula (A)

comprising reacting a compound of formula (I) with a compound of formula (II):

wherein

R 1 and R 2 are the same or different and each is independently a C 1 -C 6 alkyl group or a C 2 -C 7 acyl group, or R 1 and R 2 together form a C 1 -C 6 alkylene group;

R 3 and R 4 are the same or different and each is independently hydrogen, halogen or a C 1 -C 6 alkyl group;

R 5 and R 6 are the same or different and each is independently hydrogen, halogen or a C 1 -C 6 alkyl group;

X is CHR 7 , O or NR 7 , and R 7 is hydrogen or a C 1 -C 6 alkyl group; and

Ar is a C 6 -C 10 aryl group substituted with from 0 to 4 substituents, each of which substituents is independently halogen or a C 1 -C 6 alkyl group; and

Y is a leaving group; and/or

(ii) a process for preparing a compound of formula (B) by reducing a compound of formula (A).

17. A process according to claim 16 , which process comprises:

(a) preparing a compound of formula (B) by reducing the compound of formula (A); and

(b) further reacting the compound of formula (B) to give a compound of formula (C).

18. A process according to claim 17 , wherein step (b) is an ureation reaction.

19. A process according to claim 16 , wherein

R 1 and R 2 are methyl;

R 3 and R 4 are hydrogen;

R 5 and R 6 are hydrogen;

X is CH 2 ;

Ar is 2,4,6-trimethylphenyl; and

Q is O.

20. A process according to claim 5 , wherein Y is a leaving group which is Br, I, OMs, OTs, ONs, OAc or OTf.

21. A process according to claim 20 , wherein Y is a leaving group which is Br.

22. A process according to claim 6 , wherein the amount of the compound of formula (II) is from 1.0 to 2.5 equivalents of the compound of formula (I).

23. A process according to claim 8 , wherein the base is lithium carbonate, sodium carbonate, potassium carbonate, caesium carbonate, lithium acetate, sodium acetate or potassium acetate.

24. A process according to claim 23 , wherein the base is lithium carbonate or sodium acetate.

25. A process according to claim 9 , wherein the amount of the base is from 1.5 to 3.0 equivalents of the compound of formula (I).

26. A process according to claim 10 , wherein the solvent comprises a polar aprotic solvent.

27. A process according to claim 26 , wherein the solvent comprises acetonitrile, tetrahydrofuran or dioxane.

28. A process according to claim 12 , wherein the process comprises reacting the compound of formula (I) and the compound of formula (II) in the presence of a solvent at reflux.

29. A process according to claim 14 , wherein reducing the compound of formula (A) comprises hydrogenating the compound of formula (A) in the presence of Raney nickel.

30. A process according to claim 18 , wherein the ureation reaction is conducted by reacting a compound of formula (B) with a compound O═C═N − Z + , where Z + is a metal cation.

31. A process according to claim 30 , wherein Z + is sodium or potassium.