Hydrochloric Acid → 2-Methoxy-4-methyl-6-phenylpyridine-3-carbonitrile

HRID 1818901

Reaction equation

HRID 1818901 reaction equation
Cl[C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[C:6]([CH3:16])[C:3]=1[C:4]#[N:5].[CH3:17][O-:18].[Na+].O.Cl>COCCOC>[CH3:17][O:18][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[C:6]([CH3:16])[C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8336882-Chloro-4-methyl-6-phenylnicotinonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 218201152-Methoxy-4-methyl-6-phenylpyridine-3-carbonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-chloro4-methyl-6-phenyl-nicotinonitrile (455 mg, 1.99 mmol) was dissolved in 20 mL of DME, added with 95% sodium methoxide (1.13 g, 19.90 mmol) and then stirred at room temperature for about 1 hour. The mixture was added to cool water and was adjusted to have a pH of about 6 to 7 with 10% HCl and then extracted with ethyl acetate. A silica gel column chromatography (10% EtOAc/Hexane) was performed on the resulting residue and 370 mg (83%) of 2-methoxy-4-methyl-6-phenyl-nicotinonitrile was obtained in white solid.

Workup

  1. additionThe mixture was added
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-2a430fb9439b42139e50a1069745ef51
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Linked notes

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