US4288599A
Expired / Lapsed
US
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Process for producing pyridine derivatives having a trifluoromethyl group at β-position thereof
Assignee: Ishihara Sangyo Kaisha Ltd
•
Filing: 1980-02-26
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Granted: 1981-09-08
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Expires: 2000-02-26
Abstract
Abstract Pyridine derivatives having a trifluoromethyl group at β-position thereof are produced by reacting β-picoline with chlorine and hydrogen fluoride in a vapor phase at high temperature for a short time. The reaction condition can be mild and the yield of the object compound is increased by reacting them in the presence of a specific metal fluodie. The pyridine derivatives useful as starting materials for agricultural chemicals and medicines can be continuously obtained by a simple reaction at high yield.
Inventors
- 👤 Ryuzo Nishiyama
- 👤 Kanichi Fujikawa
- 👤 Isao Yokomichi
- 👤 Yasuhiro Tsujii
- 👤 Shigeyuki Nishimura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 01:15
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/61; C07D213/24; C07D213/26
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
49 words
A process for producing a pyridine derivative having a trifluoromethyl group at the β-position thereof and having the formula: ##STR2## wherein X and Y, respectively, are hydrogen or chloro which comprises reacting β-picoline with chlorine and hydrogen fluoride by a vapor phase reaction in the absence of a catalyst.
Claim 2
Dependent Claim
49 words
A process for producing a pyridine derivative having a trifluoromethyl group at the β-position thereof and having the formula: ##STR2## wherein X and Y, respectively, are hydrogen or chloro which comprises reacting β-picoline with chlorine and hydrogen fluoride by a vapor phase reaction in the absence of a catalyst.
Claim 3
Dependent Claim
18 words
A process according to claim 1 wherein said reaction is carried out in the presence of a diluent.
Claim 4
Dependent Claim
17 words
A process according to claim 1 wherein said reaction is carried out at 300° to 600° C.
Claim 5
Dependent Claim
24 words
A process according to claim 1, wherein the residence time of the reaction mixture in the reaction zone is from 0.5 to 50 seconds.
Claim 6
Dependent Claim
15 words
A process according to claim 1 wherein said pyridine derivative is 2-chloro-3-trifluoromethylpyridine, 2-chloro-5-trifluoromethylpyridine or 2,6-dichloro-3-trifluoromethylpyridine.
Claim 7
Dependent Claim
12 words
A process according to claim 1 wherein said pyridine derivative is 2-chloro-5-trifluoromethylpyridine.
Claim 8
Dependent Claim
12 words
A process according to claim 1 wherein said pyridine derivative is β-trifluoromethylpyridine.
Claim 9
Dependent Claim
80 words
A process for producing a pyridine derivative having a trifluoromethyl group at the β-position thereof and having the formula: ##STR3## wherein X and Y, respectively, are hydrogen or chloro which comprises reacting β-picoline with chlorine and hydrogen fluoride by a vapor phase reaction in the presence of a catalyst comprising a fluoride of a metal selected from the group consisting of aluminum, chromium, iron, nickel, cobalt, manganese, chromium with aluminum, iron with aluminum, manganese with aluminum, and cobalt with aluminum.
Claim 10
Dependent Claim
80 words
A process for producing a pyridine derivative having a trifluoromethyl group at the β-position thereof and having the formula: ##STR3## wherein X and Y, respectively, are hydrogen or chloro which comprises reacting β-picoline with chlorine and hydrogen fluoride by a vapor phase reaction in the presence of a catalyst comprising a fluoride of a metal selected from the group consisting of aluminum, chromium, iron, nickel, cobalt, manganese, chromium with aluminum, iron with aluminum, manganese with aluminum, and cobalt with aluminum.
Claim 11
Dependent Claim
18 words
A process according to claim 8, wherein said reaction is carried out in the presence of a diluent.
Claim 12
Dependent Claim
17 words
A process according to claim 8, wherein said reaction is carried out at 300° to 600° C.
Claim 13
Dependent Claim
24 words
A process according to claim 8, wherein the residence time of the reaction mixture in the reaction zone is from 0.5 to 50 seconds.
Claim 14
Dependent Claim
37 words
A process according to claim 8, wherein said reaction is carried out in the presence of a catalyst comprising a fluoride of a metal selected from the group consisting of aluminum, chromium, iron, nickel, cobalt and manganese.
Claim 15
Dependent Claim
15 words
A process according to claim 8, wherein said pyridine derivative is 2-chloro-3-trifluoromethylpyridine, 2-chloro-5-trifluoromethylpyridine or 2,6-dichloro-3-trifluoromethylpyridine.
Claim 16
Dependent Claim
12 words
A process according to claim 8, wherein said pyridine derivative is 2-chloro-5-trifluoromethylpyridine.
Claim 17
Dependent Claim
12 words
A process according to claim 8, wherein said pyridine derivative is β-trifluoromethylpyridine.
Claim 18
Dependent Claim
28 words
A process according to claim 8, wherein the catalyst is suspended in a gas flow containing the reaction mixture to carry out said reaction in a fluidized condition.
Claim 19
Dependent Claim
17 words
A process according to claim 8, wherein said catalyst is a fluoride of aluminum, iron or chromium.
References Cited (Backward Citations)
EP0000483A1
Cited
WO1979000094A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-09-07 | 1985-03-09 | 1985-09-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-07 | 1989-03-09 | 1989-09-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-07 | 1993-03-09 | 1993-09-08 | $7700.00 | Window Closed / Lapsed |