Acetic Acid → HCID 84071046, compound

HRID 2206608Notes

Reaction equation

HRID 2206608 reaction equation
Cl[C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6](Cl)[C:3]=1[C:4]#[N:5].[CH3:12][O-:13].[Na+].C[C:16]([OH:18])=O>CO>[CH3:12][O:13][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([O:18][CH3:16])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 112754712,4-DICHLORO-6-METHYLNICOTINONITRILE

Product 1

HCID 84071046HCID 84071046, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,4-dichloro-6-methylnicotinonitrile (45 g, 240 mmol) was dissolved in CH3OH (300 ml). NaOMe (30% in MeOH, 100 ml, 1680 mmol) was added. The mixture was refluxed for 4 h. After cooled to r.t., the reaction mixture was neutralized by HOAc. The solvent was removed under vacuum and the residue was washed with H2O (300 ml) and MTBE (100 ml). The resulting solid was coevaporated with dry THF (300 ml) to give 2,4-dimethoxy-6-methylnicotinonitrile as a dark-yellow solid. (40 g, yield 95%).

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. customThe solvent was removed under vacuum
  3. washthe residue was washed with H2O (300 ml) and MTBE (100 ml)

Sources & evidence

ORD record
ord-56cc2d081a1e4739b3a7c22f924fb472
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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