Formaldehyde → Pyridine, 4-ethyl-, 1-oxide

HRID 1637740Notes

Reaction equation

HRID 1637740 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)[CH3:2].[OH:9]O.C=O>C(O)(=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][N+:6]([O-:9])=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 784Hydrogen Peroxide2×HCID 108224-Ethylpyridine

Product 1

HCID 84683Pyridine, 4-ethyl-, 1-oxideYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-ethylpyridine (10.7 g, 0.10 mol) in 35 ml of acetic acid heated at 95-100° C. is treated dropwise over a 18 min period with 30% hydrogen peroxide (28 ml). After 4 h, the excess hydrogen peroxide is decomposed by the portionwise addition of paraformaldehyde (10.0 g) at the previously maintained temperature until a negative starch iodide test is obtained. The reaction mixture is cooled and concentrated at reduced pressure. The residue is chromatographed with 325 g of silica gel packed and eluted initially with acetone-chloroform-methanol (3:6.7:0.3) and thereafter with an increasing methanol gradient to obtain 10.55 g (83%) of 4-Ethylpyridine-1-oxide.

Workup

  1. customis obtained
  2. temperatureThe reaction mixture is cooled
  3. concentrationconcentrated at reduced pressure
  4. customThe residue is chromatographed with 325 g of silica gel
  5. washeluted initially with acetone-chloroform-methanol (3:6.7:0.3)

Sources & evidence

ORD record
ord-2df80ecca2cc497dac06462220beca29
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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