Sodium Methoxide → HCID 178492314, compound

HRID 1500968Notes

Reaction equation

HRID 1500968 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([OH:10])[N:5]=[C:4]([CH3:11])[CH:3]=1.[CH3:12][O-:13].[Na+]>CO>[OH:10][C:6]1[N:5]=[C:4]([CH3:11])[CH:3]=[C:2]([O:13][CH3:12])[C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178426119HCID 178426119, compound

Product 1

HCID 178492314HCID 178492314, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a pressure vessel was added 4-chloro-2-hydroxy-6-methylnicotinonitrile (337 mg, 2.0 mmol), sodium methoxide (530 mg, 10.0 mmol), methanol (15 mL), and a magnetic stirrer. The pressure vessel was sealed, and was stirred at 100° C. for 16 hours before the solvent was removed by rotary evaporation. To the residue was added water (10 mL) and ethyl acetate (50 mL). The organic layer was separated and concentrated in vacuo to provide crude product which was purified by column chromatography (silica gel, dichloromethane/methanol=40:1) to afford 2-hydroxy-4-methoxy-6-methylnicotinonitrile (70 mg, 21%) as a brown solid.

Workup

  1. customThe pressure vessel was sealed
  2. customwas removed by rotary evaporation
  3. additionTo the residue was added water (10 mL) and ethyl acetate (50 mL)
  4. customThe organic layer was separated
  5. concentrationconcentrated in vacuo
  6. customto provide crude product which
  7. customwas purified by column chromatography (silica gel, dichloromethane/methanol=40:1)

Sources & evidence

ORD record
ord-b76c08d4393c4229a5976dfb0cca9ad4
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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