US 11,028,056 B2 · Method for producing 3-arylpropionamide compound and 3-arylpropionic acid ester compound

Abstract

The present invention provides a method for industrially producing: a pyrimidine compound having pest control efficacy; 2-[4-(trifluoromethyl)phenyl]ethylamine which is a production intermediate of the pyrimidine compound; a phenylethylamine compound useful as a pharmaceutical and agrochemical intermediate; and further a 3-arylpropionamide compound and a 3-arylpropionic acid ester compound useful as production intermediates of the phenylethylamine compound. The 3-arylpropionamide compound or the 3-arylpropionic acid ester compound can be efficiently and industrially produced in a single step by reacting a compound represented by formula (1) (wherein X represents a chlorine atom or a bromine atom; and Y represents an alkyl group optionally substituted with fluorine atom(s), a hydrogen atom, a fluorine atom, a cyano group, an alkylcarbonyl group, a dialkylamino group, or the like) with acrylamide or an acrylic acid ester in the presence of a metal catalyst and a reducing agent.

Claims8

Dependent claims

A method for producing a compound represented by formula (2)

(wherein
Y represents an alkyl group optionally substituted with fluorine atom(s), an alkoxy group optionally substituted with fluorine atom(s), an alkoxyalkyl group optionally substituted with fluorine atom(s), an alkylthio group optionally substituted with fluorine atom(s), an alkylsulfonyl group optionally substituted with fluorine atom(s), a hydrogen atom, a fluorine atom, a cyano group, an alkylcarbonyl group, or a dialkylamino group;
and
Z represents a NH2
the method comprising
Step (a):
reacting a compound represented by formula (1)
(wherein X represents a chlorine atom;
and Y is the same as defined above)
with a compound represented by formula (5)
(wherein Z is the same as defined above)
in the presence of a nickel compound and zinc to produce the compound represented by formula (2).

9 more elements

A method for producing a compound represented by formula (3)

(wherein Y represents an alkyl group optionally substituted with fluorine atom(s), an alkoxy group optionally substituted with fluorine atom(s), an alkoxyalkyl group optionally substituted with fluorine atom(s), an alkylthio group optionally substituted with fluorine atom(s), an alkylsulfonyl group optionally substituted with fluorine atom(s), a hydrogen atom, a fluorine atom, a cyano group, an alkylcarbonyl group, or a dialkylamino group)
the method comprising the following Step (a-2) or Step (c), and comprising the following Step (d):
Step (a-2):
reacting a compound represented by formula (1)
(wherein X represents a chlorine atom;
and Y is the same as defined above)
with a compound represented by formula (5a)
in the presence of a nickel compound and zinc to produce a compound represented by formula (2a)
(wherein Y is the same as defined above);
or
Step (c):
the following Step (a-1) and the following Step (b)
Step (a-1):
reacting a compound represented by formula (1)
(wherein X represents a chlorine atom;
and Y is the same as defined above)
with a compound represented by formula (5b)
(wherein R2 represents a methyl group or an ethyl group)
in the presence of a nickel compound and zinc to produce a compound represented by formula (2b)
(wherein Y and R2 are the same as defined above);
and
Step (b):
reacting the compound represented by formula (2b) with formamide in the presence of a strong base to produce a compound represented by formula (2a)
(wherein Y is the same as defined above);
and
Step (d):
subjecting the compound represented by formula (2a) to a Hofmann rearrangement to produce the compound represented by formula (3).

24 more elements

Dependencies are inferred from the claim text.

Method for producing 3-arylpropionamide compound and 3-arylpropionic acid ester compound

Life of this patent

Method for producing 3-arylpropionamide compound and 3-arylpropionic acid ester compound

Life of this patent

Abstract

Claims8