Acetic Acid → HCID 53915788, compound

HRID 1350117Notes

Reaction equation

HRID 1350117 reaction equation
C(O)(=O)C.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](=[N:20]O)[CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:6]=1>C(O)C.[Zn]>[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([NH2:20])[CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[CH:6]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 85974475HCID 85974475, compound

Product 1

HCID 53915788HCID 53915788, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

Acetic acid (16 mL) was added to a suspension of 1-(3-pyridyl)-3-(4-oxanyl)propan-1-one oxime (1.60 g, 6.83 mmol) in 95% ethanol (40 mL) over a period of 15 min. Zinc dust (12 g, 180 mmol) was added and the reaction mixture was stirred at ambient temperature for 4 h. The reaction mixture was filtered through a Celite plug, which was then washed with ethanol (50 mL). The combined filtrates were concentrated by rotary evaporation. The solid residue was made basic by addition of 50% aqueous NaOH (with ice bath cooling), saturated with solid NaCl and extracted with chloroform (5×30 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated by rotary evaporation to give pure product as a colorless viscous liquid (1.40 g, 82% yield).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite plug, which
  2. washwas then washed with ethanol (50 mL)
  3. concentrationThe combined filtrates were concentrated by rotary evaporation
  4. additionThe solid residue was made basic by addition of 50% aqueous NaOH (with ice bath cooling), saturated with solid NaCl
  5. extractionextracted with chloroform (5×30 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-a0cd146571e84fbcb0c2bdd61563b1be
Source dataset
uspto-grants-2007_05
Patent number
US07214686B2

Reaction notes

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