3-Methoxyphenol → HCID 19771892, compound

HRID 1085097Notes

Reaction equation

HRID 1085097 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:17]1[N:24]=[CH:23][CH:22]=[CH:21][C:18]=1[C:19]#[N:20]>CN(C=O)C.[Cu]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][C:17]1[C:18]([C:19]#[N:20])=[CH:21][CH:22]=[CH:23][N:24]=1

Participants

6

Reactant 3

HCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 810792-Chloronicotinonitrile

Product 1

HCID 19771892HCID 19771892, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

3-Methoxyphenol (124 g) and anhydrous potassium carbonate (69 g) were heated together with stirring in dry DMF (500 ml) at 80° C. under an atmosphere of nitrogen. After 45 minutes, the greyish solution was cooled and 2-chloronicotinonitrile (138.5 g) and copper bronze (10 g) were added (washed in with 100 ml DMF). The resulting brown reaction mixture was heated to 125°-130° C. After 21/2 hours, the reaction mixture was cooled and filtered to remove excess copper bronze and undissolved solid material. The resulting solution was added to water (3 liters) and left to stand overnight. The resulting precipitate was filtered, washed with water then dissolved in ether. The ether solution was dried, filtered and evaporated to afford 2-(3-methoxyphenoxy)-3-cyanopyridine as an off-white solid (203.5 g, 90%).

Workup

  1. temperaturethe greyish solution was cooled
  2. wash(washed in with 100 ml DMF)
  3. temperatureThe resulting brown reaction mixture was heated to 125°-130° C
  4. temperatureAfter 21/2 hours, the reaction mixture was cooled
  5. filtrationfiltered
  6. customto remove excess copper bronze and undissolved solid material
  7. additionThe resulting solution was added to water (3 liters)
  8. waitleft
  9. waitto stand overnight
  10. filtrationThe resulting precipitate was filtered
  11. washwashed with water
  12. dissolutionthen dissolved in ether
  13. dry with materialThe ether solution was dried
  14. filtrationfiltered
  15. customevaporated

Sources & evidence

ORD record
ord-352ae762b7db49aa90e524a5d93e627a
Source dataset
uspto-grants-1991_04
Patent number
US05008276

Reaction notes

Loading…