Hydroxylamine → HCID 86678191, compound

HRID 1747533Notes

Reaction equation

HRID 1747533 reaction equation
C(O[CH:4]([O:13]CC)[C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[N:9][CH:10]=1)C.[NH2:16]O.O.[C:19](Cl)(=[O:21])[CH3:20]>C(O)C>[CH3:20][C:19]1[O:21][N:12]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([CH:4]=[O:13])=[CH:10][N:9]=2)[N:16]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 962WaterHCID 6367Acetyl chlorideHCID 86678192HCID 86678192, compound

Product 1

HCID 86678191HCID 86678191, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (5 mL) was dissolved 5-(diethoxymethyl)picolinonitrile (230 mg, 1.12 mmol) obtained in Step 1. A 50% aqueous hydroxylamine solution (0.368 g, 5.58 mmol) was added and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The resulting white solid was dissolved in pyridine (5 mL). Acetyl chloride (0.396 mL, 5.58 mmol) was added and the mixture was stirred at 100° C. for 12 hours. The solvent in the reaction mixture was evaporated under reduced pressure and water was added. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7) to give 6-(5-methyl-1,2,4-oxadiazol-3-yl)nicotinaldehyde (200 mg, 95% yield).

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. dissolutionThe resulting white solid was dissolved in pyridine (5 mL)
  7. stirringthe mixture was stirred at 100° C. for 12 hours
  8. customThe solvent in the reaction mixture was evaporated under reduced pressure and water
  9. additionwas added
  10. extractionExtraction with ethyl acetate
  11. washwashing with saturated brine
  12. dry with materialdrying over anhydrous sodium sulfate
  13. filtrationAfter filtration
  14. customthe solvent in the filtrate was evaporated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7)

Sources & evidence

ORD record
ord-9354eac39c014bc9a07116cfd1a18934
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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