Hydrochloric Acid → 4-(2-Hydroxyiminopropionyl)pyridine

HRID 620817Notes

Reaction equation

HRID 620817 reaction equation
[N:1](OCCC(C)C)=[O:2].C[O-].[Na+].[C:12]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)(=[O:15])[CH2:13][CH3:14].Cl>CO>[OH:2][N:1]=[C:13]([CH3:14])[C:12]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 743431-(4-Pyridinyl)-1-propanoneHCID 10942334Sodium Methoxide

Product 1

HCID 587523384-(2-Hydroxyiminopropionyl)pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of isoamyl nitrite (2.6 ml) and sodium methoxide (28% in methanol, 3.4 ml) in methanol (40 ml) was added dropwise a solution of 4-propionylpyridine (2.0 g) in methanol (10 ml) under ice-cooling. The reaction mixture was stirred at ambient temperature for 3 hours, and then neutralized with 1N hydrochloric acid. After evaporation to remove methanol, the organic layer was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate, evaporated and triturated with diisopropyl ether to give 4-(2-hydroxyiminopropionyl)pyridine (0.95 g).

Workup

  1. temperaturecooling
  2. customAfter evaporation
  3. customto remove methanol
  4. extractionthe organic layer was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customtriturated with diisopropyl ether

Sources & evidence

ORD record
ord-bb0d01142a9a4ba7b76eacf480d5f933
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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