Water → 3,5-Dimethoxypyridine

HRID 986366Notes

Reaction equation

HRID 986366 reaction equation
ClC1C=NC=C(Cl)C=1.[CH3:9][O-:10].[Na+].O.Cl[C:14]1[CH:15]=[N:16][CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1>CS(C)=O.C(OCC)C>[CH3:9][O:10][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 171533,5-DichloropyridineHCID 10942334Sodium Methoxide2×HCID 110947383-Chloro-5-methoxypyridine

Product 1

HCID 8177333,5-Dimethoxypyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

50 g of 3,5-dichloro-pyridine are dissolved in 250 ml dimethylsulfoxide. 15 g sodium methylate are added to this solution under stirring. It is stirred under exclusion of moisture at 60°-80° C. 15 g sodium methylate are further added after each of 8 and 16 hours. After a total of 72 hours' stirring, the reaction mixture is reacted with a little water and shaked out with diethylether. The ether phase, after drying, is distilled in a vacuum, resulting in 24 g (51% of theoretical amount) of 3,5-dimethoxy-pyridine in the boiling range 90°-120° C. at 1.6·103Pa. The product is polluted with a small amount of 3-chloro-5-methoxypyridine. It can, however, be employed directly in the next stage for nitrification, since the chloro-compound is not dinitrified and therefore can easily be removed upon crystallization of the 3,5-dimethoxy-2,6-dinitro-pyridine.

Workup

  1. stirringIt is stirred under exclusion of moisture at 60°-80° C
  2. stirringAfter a total of 72 hours' stirring
  3. dry with materialThe ether phase, after drying
  4. distillationis distilled in a vacuum
  5. customresulting in 24 g (51% of theoretical amount) of 3,5-dimethoxy-pyridine in the boiling range 90°-120° C. at 1.6·103Pa
  6. customcan easily be removed upon crystallization of the 3,5-dimethoxy-2,6-dinitro-pyridine

Sources & evidence

ORD record
ord-8d1b165cf62a4d6b9e60c84bdef5d7bc
Source dataset
uspto-grants-1987_12
Patent number
US04713080

Reaction notes

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