1-Acetylnaphthalene → 1-(Naphthalen-1-yl)ethanone oxime

HRID 2122100Notes

Reaction equation

HRID 2122100 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[NH2:15][OH:16]>N1C=CC=CC=1>[C:1](=[N:15][OH:16])([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 136631-AcetylnaphthaleneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3496811-(Naphthalen-1-yl)ethanone oximeYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 50 ml round-bottom flask, a mixture of acetonaphthone, hydroxylamine hydrochloride in pyridine was stirred, at room temperature under nitrogen blanket, for five days. The reaction mixture was then concentrated under vacuum to remove most of pyridine. The oil was then dissolved in dichloromethane. The product precipitated on standing. The product was obtained as a white solid in 65% yield.

Workup

  1. concentrationThe reaction mixture was then concentrated under vacuum
  2. customto remove most of pyridine
  3. dissolutionThe oil was then dissolved in dichloromethane
  4. customThe product precipitated
  5. customThe product was obtained as a white solid in 65% yield

Sources & evidence

ORD record
ord-c499d1520b644d4698af39ebe86f5379
Source dataset
uspto-grants-2004_02
Patent number
US06696608B1

Reaction notes

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