Pyrrolidinone derivative compound

Abstract

A compound represented by the following formula (12) useful as an intermediate for production of drug or agricultural chemical: (wherein R 21 to R 25 are each independently a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, a cyano group, a nitro group, an amino group, a carboxyl group, a thiol group, an alkylthio group of 1 to 4 carbon atoms or a carbamoyl group) can be produced by reacting a compound represented by the formula (13): (wherein R 21 to R 25 have the same definitions as given above) with 1,1-cyclopropanedicarboxylic acid. The compound of the formula (12) is useful as a raw material for production of a pyrrolidinone compound useful as an active ingredient of drug.

What is claimed is:  
     
         1 . A process for producing a pyrrolidinone compound represented by the formula (1):  
       
         
           
           
               
               
           
         
         [wherein R 1  is an alkyl group of 1 to 12 carbon atoms or a substituent represented by the formula (2):  
         
           
             
             
                 
                 
             
           
         
         (wherein R 2  is a hydrogen atom, a halogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, a hydroxyl group, a cyano group, an amino group, a nitro group, a carbamoyl group, a thiol group, an alkylthio group of 1 to 4 carbon atoms or a carboxyl group; p is an integer of 1 to 5; when p is 2 or more, each R 2  independently has the same definition as given above; and j is an integer of 0 to 2), and Q is a substituent represented by the formula (3a), (3b), (3c) or (3d):  
         
           
             
             
                 
                 
             
           
         
         {in the formula (3a), R 3  and R 4  are each independently a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, and R 3  and R 4  may bond to each other to form a morpholine ring; in the formula (3b), m and n are each independently an integer of 1 to 4, X is a hydrogen atom, a hydroxyl group, a cyano group, a carbamoyl group, a halogen atom or an alkyl group of 1 to 4 carbon atoms, and Y is a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group; in the formula (3c), W is an alkyl group of 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, or an alkyl group of 1 to 2 carbon atoms substituted with a substituted or unsubstituted phenyl group; and in the formula (3d), m and n are each independently an integer of 1 to 4, Z is a hydrogen atom, an alkyl group of 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group, an alkyl group of 1 to 2 carbon atoms substituted with a substituted or unsubstituted phenyl group, or a substituent represented by the formula (4):  
         —(CH 2 ) k —OR 5    (4)  
         (wherein k is an integer of 2 to 3; and R 5 is a hydrogen atom, an alkyl group of 1 to 3 carbon atoms, an alkenyl group of 2 to 3 carbon atoms or an alkynyl group of 2 to 3 carbon atoms)}],  
         which process includes a step of reacting a compound represented by the formula (5):  
         
           
             
             
                 
                 
             
           
         
         (wherein R 1  has the same definition as given above) with an amine derivative represented by the formula (6a), (6b), (6c) or (6d):  
         
           
             
             
                 
                 
             
           
         
         {in the formula (6a), R 3  and R 4  have the same definitions as given above; in the formula (6b), X, Y, m and n have the same definitions as given above; in the formula (6c), W has the same definition as given above; and in the formula (6d), Z, m and n have the same definitions as given above} in the presence of formaldehyde to produce a pyrrolidinone compound of the formula (1).  
       
     
     
         2 . A process according to  claim 1 , wherein a pyrrolidinone compound of the formula (1) {wherein R 1  is a substituent represented by the formula (2a):  
       
         
           
           
               
               
           
         
         (wherein R 2a  is a hydrogen atom or a halogen atom; p is an integer of 1 to 5; when p is 2 or more, each R 2a  independently has the same definition as given above; and j a  is 0), and Q is a substituent represented by the formula (7):  
         
           
             
             
                 
                 
             
           
         
         (wherein m and n are each independently an integer of 1 to 4; k is an integer of 2 to 3; and R 5  is a hydrogen atom, an alkyl group of 1 to 3 carbon atoms, an alkenyl group of 2 to 3 carbon atoms or an alkynyl group of 2 to 3 carbon atoms)} is produced by reacting a compound of the formula (5) {wherein R 1  is a substituent represented by the formula (2a) (wherein R 2a , p and j a  have the same definitions as give above)} with an amine derivative represented by the formula (6d) {wherein Z is a substituent represented by the formula (4) (wherein k and R 5  have the same definitions as given above)} in the presence of formaldehyde.  
       
     
     
         3 . A process according to  claim 2 , wherein a pyrrolidinone compound of the formula (1) {wherein R 1  is a 4-chlorophenyl group and Q is a substituent represented by the formula (8):  
       
         
           
           
               
               
           
         
         (wherein R 6  is an alkyl group of 1 to 3 carbon atoms)} is produced by reacting a compound of the formula (5) (wherein R 1  is a 4-chlorophenyl group) with an amine derivative represented by the formula (9):  
         
           
             
             
                 
                 
             
           
         
         (wherein R 6  has the same definition as given above) in the presence of formaldehyde.  
       
     
     
         4 . A process according to  claim 3 , wherein the amine derivative is a compound of the formula (9) wherein R 6  is a methyl group.  
     
     
         5 . A compound represented by the formula (5):  
       
         
           
           
               
               
           
         
         (wherein R 1  has the same definition as given above, with the proviso that R 1  is not any of a 2-methylphenyl group, a 3-trifluoromethylphenyl group, a 4-methoxyphenyl group and a 3,4-dichlorophenyl group); or a salt thereof.  
       
     
     
         6 . A compound of the formula (5) according to  claim 5 , wherein R 1  is represented by the formula (2) (wherein R 2  and p have the same definitions as given above, and j is 0); or a salt thereof.  
     
     
         7 . A compound of the formula (5) according to  claim 5  or  6 , wherein R 1  is a 4-chlorophenyl group; or a salt thereof.  
     
     
         8 . A process for producing a compound represented by the formula (12):  
       
         
           
           
               
               
           
         
         (wherein R 21  to R 25  are each independently a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, a cyano group, a nitro group, an amino group, a carboxyl group, a thiol group, an alkylthio group of 1 to 4 carbon atoms or a carbamoyl group) which process includes a step of reacting a compound represented by the formula (13):  
         
           
             
             
                 
                 
             
           
         
         (wherein R 21  to R 25  have the same definitions as given above) with 1,1-cyclopropanedicarboxylic acid to produce a compound of the formula (12).  
       
     
     
         9 . A process according to  claim 8 , wherein R 21 , R 22 , R 24  and R 25  are each a hydrogen atom and R 23  is a chlorine atom or a bromine atom.  
     
     
         10 . A process according to  claim 9 , wherein R 23  is a chlorine atom.