Process for the preparation of 2-chloro-5-methylpyridine

• US 4,897,488 A
• Filed: 01/04/1989
• Issued: 01/30/1990
• Est. Priority Date: 01/07/1988
• Status: Expired due to Term

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Gallenkamp, Bernd, Knops, Hans-Joachim
• Primary Examiner(s): Rotman, Alan L.
• Application Number:
  US07/293,260
• Time in Patent Office: 391 Days
• Field of Search: 546/345, 546/346
• US Class Current: 546/345
• CPC Class Codes: C07D 213/61 Halogen atoms or nitro radicals

Abstract

In the preparation of 2-chloro-5-methylpyridine of the formula ##STR1## by reacting 3-methylpyridine 1-oxide with phosphorus oxychloride, the improvement which comprises carrying out the reaction in the presence of a basic organic nitrogen compound and in the presence of a diluent at a temperature between about -50° C. and +50° C.

Claims

1. In the preparation of 2-chloro-5-methylpyridine of the formula ##STR6## by reacting 3-methylpyridine 1-oxide with phosphorus oxychloride, the improvement which comprises carrying out the reaction in the presence of a basic organic nitrogen compound and in the presence of a diluent at a temperature between about -50°

C. and +50°

C.

2. The process according to claim 1, wherein the basic organic nitrogen compound is selected from the group consisting of a dialkylamine, a trialkylamine, a dialkylcycloalkylamine, a dialkylaralkylamine and a dialkylarylamine.

3. The process according to claim 1, wherein the basic organic nitrogen compound is diisopropylamine.

4. The process according to claim 1, wherein the diluent is an inert organic solvent.

5. The process according to claim 1, wherein the diluent is methylene chloride.

6. The process according to claim 1, wherein the reaction is carried out at about -20°

C. to +20°

C.

7. The process according to claim 1, wherein about 1 to 10 moles of the basic organic nitrogen compound are used per mole of 3-methylpyridine 1-oxide.

8. The process according to claim 1, wherein the reaction mixture formed in the reaction is subjected to steam distillation.

9. The process according to claim 8, wherein the residue of the steam distillation is subjected to distillation to distill off the pure compound (I).

10. The process according to claim 8, wherein the basic organic nitrogen compound is diisopropylamine, the diluent is methylene chloride, the reaction is carried out at about -20°

C. to +20°

C. and about 1 to 10 moles of the basic organic nitrogen compound are used per mole of 3-methylpyridine 1-oxide.