Hydrochloric Acid → 2-Chloro-6-methoxy-4-methylnicotinonitrile

HRID 1818905Notes

Reaction equation

HRID 1818905 reaction equation
[Cl:1][C:2]1[N:9]=[C:8](Cl)[CH:7]=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5].[OH2:12].Cl.[CH3:14]O>>[Cl:1][C:2]1[N:9]=[C:8]([O:12][CH3:14])[CH:7]=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 962WaterHCID 701313-Cyano-2,6-dichloro-4-methylpyridine

Product 1

HCID 107499612-Chloro-6-methoxy-4-methylnicotinonitrileYield 50%

Procedure

2,6-dichloro-4-methyl-nicotinonitrile (3.70 g, 19.83 mmol) was dissolved in 30 mL of methanol, added with 4.28 mL of methanol containing 25% sodium methoxide and then stirred for about 3 hours at room temperature. The mixture was added to cool water, adjusted to have a pH of about 6 to 7 with 10% HCl and extracted using methylene chloride. The extract was dried with anhydrous sodium sulfate, filtered and evaporated under reduced pressure. A silica gel column chromatography (10% EtOAc/Hexane) was performed to obtain 1.8 g (50%) of 2-chloro-6-methoxy-4-methyl-nicotinonitrile in pale yellow solid.

Workup

  1. additionThe mixture was added
  2. extractionextracted
  3. dry with materialThe extract was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-02fe246955b7443d94e8005501ba50e1
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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