Sodium Methoxide → HCID 178492314, compound

HRID 1501218Notes

Reaction equation

HRID 1501218 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 were added 4-chloro-2-hydroxy-6-methylnicotinonitrile (337 mg, 2.0 mmol), sodium methanolate (540 mg, 10.0 mmol), methanol (15 mL), and magnetic stirrer. The pressure vessel was sealed, and it was stirred at 100° C. for 16 hours. After being cooled to room temperature, the vessel was opened, and the reaction solution was transferred to an eggplant-shaped bottle. The solvent was removed by rotary evaporation. To the residue was added water (10 mL) and ethyl acetate (50 mL). The layers were separated. The organic phase was concentrated in vacuo to provide crude product which was purified by silica gel column chromatography with dichloromethane/methanol=10:1 to afford 2-hydroxy-4-methoxy-6-methylnicotinonitrile (70 mg, 21%) as a brown solid.

Workup

  1. customThe pressure vessel was sealed
  2. temperatureAfter being cooled to room temperature
  3. customThe solvent was removed by rotary evaporation
  4. additionTo the residue was added water (10 mL) and ethyl acetate (50 mL)
  5. customThe layers were separated
  6. concentrationThe organic phase was concentrated in vacuo
  7. customto provide crude product which
  8. customwas purified by silica gel column chromatography with dichloromethane/methanol=10:1

Sources & evidence

ORD record
ord-b23749eae1a94ee1a662da59294fa251
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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