Pyridine → Cyclooctanone, oxime

HRID 976617Notes

Reaction equation

HRID 976617 reaction equation
[C:1]1(=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:11][OH:12].N1C=CC=CC=1>C(O)C>[C:1]1(=[N:11][OH:12])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10403CyclooctanoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 136841Cyclooctanone, oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing cyclooctanone (12.6 g, 0.1 mol) and hydroxylamine hydrochloride (14.0 g, 0.2 mole) in a mixture of pyridine (40 mL, 0.5 mole) and ethanol (50 mL) was stirred at ambient temperature for about 15 hours. The solvent was then removed by rotary evaporation. The residue was dissolved in diethyl ether (300 mL) then washed with hydrochloric acid (2×100 mL). The aqueous layer was extracted with diethyl ether (2×150 mL). The ether extracts were combined, dried over magnesium sulfate then concentrated to provide cyclooctanone oxime as a white solid.

Workup

  1. customThe solvent was then removed by rotary evaporation
  2. dissolutionThe residue was dissolved in diethyl ether (300 mL)
  3. washthen washed with hydrochloric acid (2×100 mL)
  4. extractionThe aqueous layer was extracted with diethyl ether (2×150 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationthen concentrated

Sources & evidence

ORD record
ord-47ac1363aded418fa0b35f27db480d5e
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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