Pyridine → HCID 87132497, compound

HRID 657685Notes

Reaction equation

HRID 657685 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=O)[CH:7]([CH2:12][C:13]#[CH:14])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:16][OH:17].N1C=CC=CC=1>C(O)C>[C:1]([CH:5]1[CH2:10][CH2:9]/[C:8](=[N:16]/[OH:17])/[CH:7]([CH2:12][C:13]#[CH:14])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 61749321HCID 61749321, compound

Product 1

HCID 87132497HCID 87132497, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-tert-butyl-2-prop-2-ynyl-cyclohexanone (50 mg, 0.26 mmol) (prepared as described in Dufey, P.; Bull. Soc. Chim. Fr.; 1968, 4653-4662) in 1.0 mL of ethanol was refluxed with hydroxylamine hydrochloride (25 mg, 0.36 mmol) and pyridine (0.25 mL, excess) for 3 h. The mixture was then allowed to cool to room temperature and partitioned between ethyl acetate and 3N aq. HCl. The organic layers were washed with saturated aqueous sodium chloride solution, dried over MgSO4, filtered and concentrated to give the titled compound as a light yellow solid (50 mg, 93% yield).

Workup

  1. custompartitioned between ethyl acetate and 3N aq. HCl
  2. washThe organic layers were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c728c37630f544d493c06ca02d84365b
Source dataset
uspto-grants-2011_12
Patent number
US08076344B2

Reaction notes

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