Pyridine → 1-Phenyl-1-cyclopentanecarboxaldehyde oxime

HRID 975265

Reaction equation

HRID 975265 reaction equation
[C:1]1([C:7]2([CH:12]=O)[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[OH:15][NH3+:16].N1C=CC=CC=1>C(O)C>[C:1]1([C:7]2([CH:12]=[N:16][OH:15])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 21645Hydroxylamine HClHCID 110951241-Phenylcyclopentane-1-carbaldehyde

Product 1

HCID 736783341-Phenyl-1-cyclopentanecarboxaldehyde oximeYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the above aldehyde (3.4 g, 20 mmol) and hydroxylammonium chloride (2.9 g, 42 mmol) in a mixture of absolute ethanol (30 ml) and pyridine (3.3 g, 42 mmol) was heated at reflux for 2 h. The solvent was evaporated in vacuo, the residue was treated with absolute ethanol (50 ml) and the suspension filtered. The solvent was evaporated from the filtrate in vacuo and the residue crystallised from a 4/1 mixture of n-heptane and ethyl acetate to give 2.5 g of 1-phenyl-1-cyclopentanecarboxaldehyde oxime.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customThe solvent was evaporated in vacuo
  4. additionthe residue was treated with absolute ethanol (50 ml)
  5. filtrationthe suspension filtered
  6. customThe solvent was evaporated from the filtrate in vacuo
  7. customthe residue crystallised from a 4/1 mixture of n-heptane and ethyl acetate

Sources & evidence

ORD record
ord-4915c322d95c4864aebbd6f6a4943ce2
Source dataset
uspto-grants-1997_03
Patent number
US05608069

Linked notes

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