Process for producing pyridazinone compound and production intermediates thereof

Patent metadata

Field	Value
Publication number	US-9650347-B2
Application number	US-201414767533-A
Country	US
Kind code	B2
Filing date	Feb 18, 2014
Priority date	Feb 21, 2013
Publication date	May 16, 2017
Grant date	May 16, 2017

Abstract

The present invention provides a process for producing a compound of the formula (1) wherein X represents a hydrogen atom, etc., and Y represents a hydrogen atom, etc., which comprises step 1 of reacting a compound of the formula (2) and a compound of the formula (3) in the presence of a Lewis acid wherein R represents a hydrogen atom, etc., to obtain an adduct, and step 2 of reacting the adduct obtained in the step 1 and hydrazine to obtain the compound of the formula (1).

First claim

The invention claimed is:

1. A compound of the formula (4);

wherein X represents a hydrogen atom, a fluorine atom, a chlorine atom or a bromine atom, Y represents a hydrogen atom, a fluorine atom, a chlorine atom or a bromine atom, and R represents a hydrogen atom or a C1-C4 alkyl group.

2. A process for producing a compound of the formula (1);

wherein X represents a hydrogen atom, a fluorine atom, a chlorine atom or a bromine atom, and Y represents a hydrogen atom, a fluorine atom, a chlorine atom or a bromine atom;
which comprises step 1 of reacting a compound of the formula (2) and a compound of the formula (3) in the presence of a Lewis acid to obtain an adduct;

wherein R represents a hydrogen atom or a C1-C4 alkyl group and X has the same meaning as defined above,

wherein Y has the same meaning as defined above;
and step 2 of reacting the adduct obtained in the step 1 and hydrazine.

3. The process according to claim 2 , wherein the adduct is a compound of the formula (5);

wherein X and Y have the same meanings as defined above.

4. The process according to claim 2 , wherein the reaction of the compound of the formula (2) and the compound of the formula (3) is conducted in the presence of a polar aprotic solvent.

5. The process according to any one of claims 2 to 4 , wherein the Lewis acid is a titanium compound or a boron compound.

6. The process according to claim 2 , 3 or 4 , wherein the reactions both in step 1 and step 2 are carried out in the presence of an aromatic hydrocarbon solvent.

7. A process for producing a compound represented by the formula (1);

wherein X represents a hydrogen atom, a fluorine atom, a chlorine atom or a bromine atom, and Y represents a hydrogen atom, a fluorine atom, a chlorine atom or a bromine atom;
which comprises reacting a compound of the formula (4) and hydrazine;

wherein R represents a hydrogen atom or a C1-C4 alkyl group and X and Y have the same meanings as defined above.

8. The process according to claim 7 , wherein the reaction is carried out in the presence of an aromatic hydrocarbon solvent.

9. A process according to claim 7 , which further comprises reacting the compound of formula (1) and a chlorinating agent to produce a compound of the formula (6);

wherein X and Y are the same as defined for formula (1).

10. A process for producing a compound of the formula (4);

wherein X represents a hydrogen atom, a fluorine atom, a chlorine atom or a bromine atom, Y represents a hydrogen atom, a fluorine atom, a chlorine atom or a bromine atom, and R represents a hydrogen atom or a C1-C4 alkyl group;
which comprises reacting a compound of the formula (2) and a compound of the formula (3) in the presence of a Lewis acid in range of from 20 to 80° C.;

wherein X and R have the same meanings as defined above,

wherein Y has the same meaning as defined above.

11. The process according to claim 10 , wherein the Lewis acid is a titanium compound or a boron compound.

12. The process according to claim 10 or 11 , wherein the reaction is carried out in the presence of an aromatic hydrocarbon solvent.

13. The process according to claim 3 , wherein the reaction of the compound of the formula (2) and the compound of the formula (3) is conducted in the presence of a polar aprotic solvent.

14. The process according to claim 5 , wherein the reactions both in step 1 and step 2 are carried out in the presence of an aromatic hydrocarbon solvent.

Assignees

• Sumitomo Chemical Co

Inventors

• Nakae Yasuyuki
• Manabe Akio
• Miyamoto Takashi

Classifications

• C07C69/675

  of saturated hydroxy-carboxylic acids · CPC title

• C07C67/475

  by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of [IMAGE cpc-sch-C07C-0963.gif] groups between different molecules · CPC title

• C07C59/88

  containing halogen · CPC title

• C07D237/12 Primary

  Halogen atoms or nitro radicals · CPC title

• C07D237/14 Primary

  Oxygen atoms · CPC title