Water → HCID 13567769, compound

HRID 2375904Notes

Reaction equation

HRID 2375904 reaction equation
[I:1][C:2]1[C:3]([OH:11])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[H-].[Na+].[CH3:14]I.O>C1COCC1>[I:1][C:2]1[C:3](=[O:11])[N:4]([CH3:14])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178526840HCID 178526840, compound

Product 1

HCID 13567769HCID 13567769, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-iodo-5-nitropyridin-2-ol (2.66 g, 10.0 mmol) in THF (30 mL) was cooled to −20° C. NaH (60% dispersion in mineral oil, 0.600 g, 15.0 mmol) was added cautiously in three portions. After being stirred for 30 min at this temperature, methyl iodide (6.23 mL, 100.0 mmol) was added dropwise through a syringe. The resulting mixture was allowed to warm to rt during a 30 min period. Stirring was continued for 18 h at rt. Water (15 mL) was added with caution to quench the reaction. THF was removed under reduced pressure and methylene chloride (80 mL) was added to the aqueous phase. Layers were separated and the aqueous phase was extracted with methylene chloride (2×50 mL). The combined organic phases were dried over MgSO4, filtered, and concentrated to afford the desired product as a yellow crystalline solid. 1H-NMR (CDCl3, 400 MHz): δ=3.73 (s, 3H), 8.65 (d, J=2.8 Hz, 1H), 8.74 (d, J=2.8 Hz, 1H). MS (ES+): m/z 280.96 [MH+]. HPLC: tR=2.55 min (ZQ2000, polar—5 min).

Workup

  1. additionwas added dropwise through a syringe
  2. customto quench
  3. customthe reaction
  4. customTHF was removed under reduced pressure and methylene chloride (80 mL)
  5. additionwas added to the aqueous phase
  6. customLayers were separated
  7. extractionthe aqueous phase was extracted with methylene chloride (2×50 mL)
  8. dry with materialThe combined organic phases were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-403b6aaa0cde4fbda444fe8b9cb38193
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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