Method for manufacturing 3-(alkylsulfonyl)pyridine-2-carboxylic acid

Patent metadata

Field	Value
Publication number	US-9850209-B2
Application number	US-201515318517-A
Country	US
Kind code	B2
Filing date	Jun 22, 2015
Priority date	Jun 26, 2014
Publication date	Dec 26, 2017
Grant date	Dec 26, 2017

Abstract

A 3-(alkylsulfonyl)pyridine-2-carboxylic acid or a salt thereof can be manufactured by comprising:
allowing a compound represented by formula (1-N):

wherein X represents a halogen atom,
to react with a compound represented by formula (2):

R 2 SM 2   (2)

wherein R 2 represents a C 1-8 straight-chain alkyl group, and M 2 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (3-N):

wherein R 2 and X are as defined above;
allowing the compound (3-N) to react with hydrogen peroxide in the presence of a tungsten catalyst and an acid;
reducing the product in the presence of a base and a heterogeneous transition metal catalyst;
and hydrolyzing the product in the presence of a base.

First claim

The invention claimed is:

1. A method for producing a compound represented by formula (7) or a salt thereof, comprising:
a step of allowing a compound represented by formula (1-N):

wherein X represents a halogen atom,
to react with a compound represented by formula (2):
R 2 SM 2   (2)

wherein R 2 represents a C 1-8 straight-chain alkyl group, and M 2 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (3-N):

wherein R 2 and X are as defined above;
a step of allowing the compound represented by formula (3-N) to react with hydrogen peroxide in the presence of a tungsten catalyst and an acid to give a compound represented by formula (6-N):

wherein R 2 and X are as defined above;
a step of reducing the compound represented by formula (6-N) in the presence of a base and a heterogeneous transition metal catalyst to give a compound represented by formula (8-N):

wherein R 2 is as defined above; and
a step of hydrolyzing the compound represented by formula (8-N) in the presence of a base to give a compound represented by formula (7) or a salt thereof:

wherein R 2 is as defined above.

2. A method for producing a compound represented by formula (8-N), comprising:
a step of allowing a compound represented by formula (1-N):

wherein X represents a halogen atom,
to react with a compound represented by formula (2):
R 2 SM 2   (2)

wherein R 2 represents a C 1-8 straight-chain alkyl group, and M 2 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (3-N):

wherein R 2 and X are as defined above;
a step of allowing the compound represented by formula (3-N) to react with hydrogen peroxide in the presence of a tungsten catalyst and an acid to give a compound represented by formula (6-N):

wherein R 2 and X are as defined above; and
a step of allowing the compound represented by formula (6-N) to react in the presence of a base and a heterogeneous transition metal catalyst to give a compound represented by formula (8-N):

wherein R 2 is as defined above.

3. A method for producing a compound represented by formula (6-N), comprising:
a step of allowing a compound represented by formula (1-N):

wherein X represents a halogen atom,
to react with a compound represented by formula (2):
R 2 SM 2   (2)

wherein R 2 represents a C 1-8 straight-chain alkyl group, and M 2 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (3-N):

wherein R 2 and X are as defined above; and
a step of allowing the compound represented by formula (3-N) to react with hydrogen peroxide in the presence of a tungsten catalyst and an acid to give a compound represented by formula (6-N):

wherein R 2 and X are as defined above.

4. A method for producing a compound represented by formula (3-N), comprising a step of allowing a compound represented by formula (1-N):

wherein X represents a halogen atom,
to react with a compound represented by formula (2):
R 2 SM 2   (2)

wherein R 2 represents a C 1-8 straight-chain alkyl group, and M 2 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (3-N):

wherein R 2 and X are as defined above.

5. A compound represented by formula (3-N):

wherein R 2 represents a C 1-8 straight-chain alkyl group, and X represents a halogen atom.

6. A compound represented by formula (6-N):

wherein R 2 represents a C 1-8 straight-chain alkyl group, and X represents a halogen atom.

Assignees

• Sumitomo Chemical Co

Inventors

• Kimura Takahiro
• Maehata Ryota

Classifications

• C07D213/79

  Acids; Esters · CPC title

• C07B61/00 Primary

  Other general methods · CPC title

• C07D213/78

  Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07D213/807 Primary

  by oxidation of pyridines or condensed pyridines · CPC title

• C07D213/803 Primary

  Processes of preparation · CPC title