Pyridine → Cyclohexanecarbaldehyde oxime

HRID 1728360Notes

Reaction equation

HRID 1728360 reaction equation
[CH:1]1([CH:7]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:10][OH:11].N1C=CC=CC=1>C(O)C>[CH:1]1([CH:7]=[N:10][OH:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 16275CyclohexanecarboxaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 638165Cyclohexanecarbaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of cyclohexanecarboxaldehyde (11.2 g, 100 mmol), hydroxylamine hydrochloride (7.2 g, 104 mmol) and pyridine (8.5 mL) in ethanol (150 mL) was stirred for 18 hours, then concentrated in vacuo. The residue was taken up in 10% aqueous citric acid and extracted with ethyl acetate (3×150 mL). The organics were combined, dried over MgSO4 and concentrated to afford cyclohexanecarboxaldehyde oxime which was used directly in the next step.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate (3×150 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-66c7493809b4484890ea368abe1630cc
Source dataset
uspto-grants-1994_07
Patent number
US05326787

Reaction notes

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