# US 2014/0194629 A1 · Nitrogen-containing heterocyclic compound and method for producing same

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- Number: US 2014/0194629 A1
- Document ID: US20140194629A1
- Status: Published application
- Kind: A1
- Application number: 14/175,958
- Filed: 2014-02-07
- Published: 2014-07-10
- Earliest claimed: 2010-04-06
- Assignees: Nippon Soda Co., Ltd.
- Applicants: Nippon Soda Co., Ltd.
- Inventors: Koichi KUTOSE; Hiroki INOUE; Shiro TSUBOKURA
- Web page: https://patentgrep.com/patent/US20140194629A1

## CPC

- C07D 213/89: with hetero atoms directly attached to the ring nitrogen atom
- C07D 213/75: Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

There are provided a nitrogen-containing heterocyclic compound such as a substituted amino-pyridine-N-oxide compound represented by formula (1), which is useful as a synthetic intermediate for an agrochemical and the like; and a method for producing the nitrogen-containing heterocyclic compound. (In formula (1), R1 and R2 each represents a hydrogen atom or an unsubstituted or substituted alkyl group; R3 represents a hydrogen atom, an unsubstituted or substituted alkylcarbonyl group or the like; R4 represents an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group or the like; A represents a hydroxyl group, a thiol group or the like; m represents any one of integers of 1 to 4; k represents any one of integers of 0 to 3; and k+m≦4.)

## Claims

### Claim at position 1

1-20. (canceled)

### Claim 21

A method for producing a compound represented by formula (13) comprising reacting a compound represented by formula (9) with a halogenating agent in a presence of a compound represented by formula (12).
wherein each of R1 and R2 independently represents a hydrogen atom, or an unsubstituted or substituted alkyl group, and R1 and R2 may form a ring together,
R6 represents an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, an unsubstituted or substituted heteroarylcarbonyl group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted alkylsulfonyl group, or an unsubstituted or substituted arylsulfonyl group,
R8 represents an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted alkoxycarbonyl group,
A represents a hydroxyl group, a thiol group, an amino group, a nitro group, a halogen atom or an organic group,
m represents any one of integers of 1 to 4,
k represents any one of integers of 0 to 3,
wherein k+m≦4,
X represents a halogen atom, and
X1 represents a chlorine atom or a bromine atom.

### Claim 22 (depends on 21)

The method according to claim 21, wherein the reaction is carried out in a presence of a halogen ion source that is soluble in an organic solvent.

### Claim 23 (depends on 22)

The method according to claim 22, wherein the halogen ion source that is soluble in an organic solvent is a halogenated ammonium salt or a halogenated phosphonium salt.

### Claim 24 (depends on 22)

The method according to claim 22, wherein the halogen ion source that is soluble in an organic solvent is a tertiary or quaternary alkyl ammonium halide salt having an alkyl group of C2 or more, or an alkyl phosphonium halide salt having an alkyl group of C2 or more.

### Claim 25 (depends on 21)

The method according to claim 21,
wherein the halogenating agent is at least one selected from the group consisting of thionyl chloride, thionyl bromide, phosphorus oxychloride, sulfuryl chloride, phosgene, diphosgene and triphosgene.

### Claim 26 (depends on 22)

The production method according to claim 22,
wherein the halogenating agent is at least one selected from the group consisting of thionyl chloride, thionyl bromide, phosphorus oxychloride, sulfuryl chloride, phosgene, diphosgene and triphosgene.

### Claim 27 (depends on 23)

The production method according to claim 23,
wherein the halogenating agent is at least one selected from the group consisting of thionyl chloride, thionyl bromide, phosphorus oxychloride, sulfuryl chloride, phosgene, diphosgene and triphosgene.

### Claim 28 (depends on 24)

The production method according to claim 24,
wherein the halogenating agent is at least one selected from the group consisting of thionyl chloride, thionyl bromide, phosphorus oxychloride, sulfuryl chloride, phosgene, diphosgene and triphosgene.