# US 5,705,656 A · N-alkylation method of pyrazole

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,705,656 A
- Document ID: US5705656A
- Status: Granted
- Kind: A
- Application number: 08/662,251
- Filed: 1996-06-14
- Granted: 1998-01-06
- Earliest claimed: 1995-06-21
- Assignees: Nissan Chemical Industries, Ltd.
- Inventors: Yoshio Ono
- Web page: https://patentgrep.com/patent/US5705656A

## CPC

- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 233/56: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

An N-alkylation method of pyrazole in which (III) is produced from (I) and (II), which is characterized by using a crystalline aluminosilicate or a crystalline aluminophosphate as a catalyst: ##STR1## wherein each of R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, alkyl, alkenyl or phenyl, R represents alkyl and Q represents hydrogen, alkyl or COOR. This is an industrially markedly useful method, because (III) can be obtained with a high yield under mild reaction conditions, and by-products including salts are not at all formed.

## Claims

### Claim 1

A method for producing an N-alkylpyrazole compound represented by the formula (III): ##STR6## wherein each of R.sup.1, R.sup.2 and R.sup.3 is independently selected from the group consisting of a hydrogen atom, a C.sub.1-20 alkyl group, a C.sub.2-20 alkenyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclopropylmethyl group, a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a benzyl group, a 1-phenethyl group, a 2-phenethyl group, a 3-phenylpropyl group, a cinnamyl group, and a phenyl group, from a pyrazole compound represented by the formula (I): ##STR7## wherein each of R.sup.1, R.sup.2 and R.sup.3 is as defined in the formula (III) above, and an alcoholic compound represented by the formula (II):
R--O--Q (II)
wherein R represents a C.sub.1-20 alkyl group and Q represents a hydrogen atom, a C.sub.1-20 alkyl group or a COOR group, wherein N-alkylation of said pyrazole compound is carried out using a crystalline aluminosilicate or a crystalline aluminophosphate as a catalyst.

### Claim 2 (depends on 1)

The method according to claim 1 wherein the catalyst has a pore size of 0.7 to 1.0 nm.

### Claim 3 (depends on 1)

The method according to claim 1 wherein the catalyst has a solid acidity.

### Claim 4 (depends on 1)

The method according to claim 1 wherein the catalyst has a proton as the cation.

### Claim 5 (depends on 1)

The method according to claim 1 wherein the catalyst has a divalent or trivalent metal ion as the cation.

### Claim 6 (depends on 1)

The method according to claim 1 wherein the catalyst is a crystalline aluminosilicate.

### Claim 7 (depends on 6)

The method according to claim 6 wherein the crystalline aluminosilicate has a pore size of 0.7 to 1.0 nm.

### Claim 8 (depends on 7)

The method according to claim 7 wherein the crystalline aluminosilicate contains a proton as the cation.

### Claim 9 (depends on 8)

The method according to claim 8 wherein the crystalline aluminosilicate has a crystal structure of faujasite.

### Claim 10 (depends on 8)

The method according to claim 8 wherein the crystalline aluminosilicate has a crystal structure of EMT.

### Claim 11 (depends on 8)

The method according to claim 8 wherein the crystalline aluminosilicate has a crystal structure of beta.

### Claim 12 (depends on 6)

The method according to claim 6 wherein the catalyst has a divalent or trivalent metal ion as the cation.

### Claim 13 (depends on 12)

The method according to claim 12 wherein the crystalline aluminosilicate has a crystal structure of faujasite.

### Claim 14 (depends on 12)

The method according to claim 12 wherein the crystalline aluminosilicate has a crystal structure of EMT.

### Claim 15 (depends on 1)

The method according to claim 1 wherein the catalyst is a crystalline aluminophosphate.

### Claim 16 (depends on 1)

The method according to claim 1 wherein each of R.sup.1, R.sup.2 and R.sup.3 independently represents a hydrogen atom, a C.sub.1-20 alkyl group, a C.sub.2-20 alkenyl group or a phenyl group.

### Claim 17 (depends on 1)

The method according to claim 1 wherein each of R.sup.1, R.sup.2 and R.sup.3 independently represents a hydrogen atom or a methyl group.

### Claim 18 (depends on 1)

The method according to claim 1 wherein R represents a C.sub.1-4 alkyl group.

### Claim 19 (depends on 1)

The method according to claim 1 wherein R represents a methyl group.

### Claim 20 (depends on 1)

The method according to claim 1 wherein Q represents a hydrogen atom.

### Claim 21 (depends on 20)

The method according to claim 20 wherein R represents a C.sub.1-4 alkyl group and each of R.sup.1, R.sup.2 and R.sup.3 independently represents a hydrogen atom or a methyl group.

### Claim 22 (depends on 20)

The method according to claim 20 wherein R represents a methyl group and each of R.sup.1, R.sup.2 and R.sup.3 independently represents a hydrogen atom or a methyl group.