Sodium Methoxide → HCID 178494181, compound

HRID 2206614Notes

Reaction equation

HRID 2206614 reaction equation
Cl[C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([OH:11])[C:3]=1[C:4]#[N:5].[CH3:12][O-:13].[Na+]>CO>[OH:11][C:6]1[C:3]([C:4]#[N:5])=[C:2]([O:13][CH3:12])[N:9]=[C:8]([CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178429078HCID 178429078, compound

Product 1

HCID 178494181HCID 178494181, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-chloro-4-hydroxy-6-methylnicotinonitrile (2.0 g, 11.9 mmol), sodium methanolate (3.2 g, 59.5 mmol) in methanol (20 mL) was stirred at 60° C. overnight under N2. The mixture was quenched with HCl (1M) to pH=2. It was partitioned between water (500 mL) and ethyl acetate (500 mL), the organic layer was dried and concentrated to afford 4-hydroxy-2-methoxy-6-methylnicotinonitrile (2.0 g brown solid, 100% yield).

Workup

  1. customThe mixture was quenched with HCl (1M) to pH=2
  2. customIt was partitioned between water (500 mL) and ethyl acetate (500 mL)
  3. customthe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3b45ad59582343a1b06c0a870144f366
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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