Water → HCID 18005197, compound

HRID 1603771Notes

Reaction equation

HRID 1603771 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.Cl[C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][N+:12]=1[O-:20].O>C1COCC1>[N+:17]([C:15]1[CH:14]=[CH:13][N+:12]([O-:20])=[C:11]([O:3][C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:16]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 844332-Chloro-4-nitropyridine 1-oxide

Product 1

HCID 18005197HCID 18005197, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.27 g of an 80% dispersion in oil, 9 mmol) was added to a solution of 3-hydroxypyridine (0.854 g, 9 mmol) in THF (3 ml) at 0° C. The mixture was then stirred for 1 h at room temperature before 2-chloro-4-nitropyridine-N-oxide* (2 g, 9 mmol) was added. The resulting solution was heated at reflux for 16 h, cooled, poured into water (100 ml) and extracted with dichloromethane (3×100 ml). The combined extracts were dried (Na2SO4) and evaporated. The residue was chromatographed on silica using ethyl acetate as eluant to afford the title compound (1.74 g, 83%) as a solid.

Workup

  1. additionwas added
  2. temperatureThe resulting solution was heated
  3. temperatureat reflux for 16 h
  4. temperaturecooled
  5. extractionextracted with dichloromethane (3×100 ml)
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. customevaporated
  8. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-8feb354a8e054553a69e3dbf65ae3136
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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