Claims
- 1. A process for the preparation of a compound of formula I wherein R and R1 are each independently H or C1-C4alkyl; R2 and R3 are each independently H, C1-C4alkyl or R2 and R3 may be taken together with the atom to which they are attached to form a group C═NOR9 or C═O; R4, R5, R6, R7, R8 and R9 are each independently H or C1-C4alkyl; and m is 0 or 1 which process comprises reacting a compound of formula II wherein Hal is Cl, Br or I and R, R1, R2, R3, R4, R5, R6, R7, R8 and m are as described hereinabove with a catalytic amount of a transition metal catalyst and at least two molar equivalents of ammonium formate in the presence of a polar solvent optionally at an elevated temperature.
- 2. The process according the claim 1 wherein the solvent is a C1-C6alkanol, a C1-C6carboxylic acid, or a mixture therof.
- 3. The process according to claim 1 wherein the transition metal is Pd.
- 4. The process according to claim 1 wherein Hal is Cl.
- 5. The process according to claim 1 wherein the temperature is about 25° C.-200° C.
- 6. The process according to claim 1 wherein m is O and R2 and R3 are each independently C1-C4alkyl.
- 7. The process according to claim 1 wherein m is 1; R2 and R3 are taken together with the atom to which they are attached to form a group C═NOR9; and R9 is C1-C4alkyl.
- 8. The process according to claim 4 wherein R1, R2 and R3 are methyl; R6, R7 and R8 are H; and m is O.
- 9. The process according to claim 4 wherein R1 is methyl; R2 and R3 are taken together with the atom to which they are attached to form a group C═NOR9; R9 is methyl; R4, R5, R6, R7 and R8 are H; and m is 1.
- 10. The process according to claim 5 wherein the temperature is about 50° C.-150° C.
- 11. A process for the preparation of a herbicidal compound of formula V or formula VII whereinR1, R2, R4, R5, R6, R7, R8, R9 and R11 are each independently H or C1-C4alkyl; R2 and R3 are each independently H or C1-C4alkyl or R2 and R3 may be taken together with the atom to which they are attached to form a group C═NOR9 or C═O; R10 is C1-C4alkyl; R12 is C1-C6alkyl or phenyl optionally substituted with one to three halogen, NO2, C1-C4alkyl or C1-C4alkoxy groups; and m is 0 or 1 which process comprises the following steps:(a) reacting a compound of formula II wherein Hal is Cl, Br, or I with a catalytic amount of a transition metal catalyst and at least two molar equivalents of ammonium formate in the presence of a polar solvent optionally at an elevated temperature to give a compound of formula I (b) hydrolyzing said formula I compound wherein R is C1-C4alkyl with base to give the corresponding carboxylic acid; and (c) reacting said carboxylic acid with a compound of formula IV to obtain the desired herbicidal compound of formula V, optionally reacting said formula V compound with a sulfonyl chloride R12SO2Cl to obtain the desired herbicidal compound of formula VII.
- 12. The process according to claim 11 wherein the transition metal catalyst in step a is Pd.
- 13. The process according to claim 12 wherein the polar solvent in step a is a C1-C6alkanol; a C1-C6carboxylic acid; or a mixture thereof.
- 14. The process according to claim 13 for the preparation of a formula V or formula VII herbicidal compound wherein m is 1; R2 and R3 are taken together with the atom to which they are attached to form a group C═NOR9; and R9 is C1-C4alkyl.
- 15. The process according to claim 13 for the preparation of a formula V or formula VII herbicidal compound wherein m is 0; and R2 and R3 are each independently C1-C4alkyl.
Parent Case Info
This application claims the benefit of Provisional application 60/128,009 filed Apr. 6, 1999.
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Number |
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Date |
Kind |
5506194 |
Nasuno et al. |
Apr 1996 |
|
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Foreign Referenced Citations (1)
Number |
Date |
Country |
WO 9708164 |
Mar 1997 |
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Non-Patent Literature Citations (1)
Entry |
Anwer, M.K. and Spatola, A.F., Tetrahedron Letters, 26 (11), pp. 1391-1384 (1985). |
Provisional Applications (1)
|
Number |
Date |
Country |
|
60/128009 |
Apr 1999 |
US |