Sodium Chloride → HCID 22989731, compound

HRID 1168936Notes

Reaction equation

HRID 1168936 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[N:7][CH:8]=1.[H-].[Na+].[Cl:12][CH2:13][CH2:14][CH2:15]I.[Na+].[Cl-]>CN(C=O)C.O>[Cl:12][CH2:13][CH2:14][CH2:15][O:9][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[N:7][CH:6]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 138083715-Methoxypyridin-3-ol

Product 1

HCID 22989731HCID 22989731, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of 5-methoxypyridin-3-ol (0.50 g, 4.01 mmol) in DMF (10 mL) was slowly added over 10 min to a cold (0-5° C.), stirring slurry of sodium hydride (0.19 g of an 80% dispersion in mineral oil, 6.33 mmol) in DMF (15 mL). The mixture was allowed to warm to ambient temperature and further stirred for 1 h. To this slurry was added drop-wise over 5 min, 1-chloro-3-iodopropane (0.98 g, 4.81 mmol), and the resulting dark brown mixture was stirred at ambient temperature for 4 h. Cold water (25 mL) was carefully added, followed by saturated NaCl solution (25 mL). The resulting mixture was extracted with ether (4×50 mL). The combined ether extracts were dried (MgSO4), filtered, and concentrated by rotary evaporation producing a dark-brown oil (0.75 g, 92.8%).

Workup

  1. additionTo this slurry was added drop-wise over 5 min
  2. extractionThe resulting mixture was extracted with ether (4×50 mL)
  3. dry with materialThe combined ether extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-420962b7fde743409b0878abe915e447
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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