Sodium Methoxide → HCID 178492314, compound

HRID 2206481Notes

Reaction equation

HRID 2206481 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-e7803b1f6ea54bb3bdca91d511ab86fe
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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