1-(2-Naphthyl)propan-1-one → 1-(2-Naphthalenyl)-1-propanone oxime

HRID 635629Notes

Reaction equation

HRID 635629 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=O)[CH2:12][CH3:13].Cl.[NH2:16][OH:17]>N1C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[N:16][OH:17])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 805871-(2-Naphthyl)propan-1-oneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 862061451-(2-Naphthalenyl)-1-propanone oximeYield 89.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.1 g (11.41 mmol) of 1-(2-naphthyl)-1-propanone and 2.1 g (30.22 mmol) of hydroxylamine hydrochloride was heated under reflux in 30 ml of pyridine for 1 hour. The solution was evaporated to dryness and the residue was partitioned between water and diethyl ether. The organic layer was washed twice with 2M hydrochloric acid, dried over magnesium sulphate, filtered and evaporated to dryness to give 2.04 g of 1-(2-naphthyl)-1-propanone oxime as a pink solid, 1H NMR (400 MHz, CDCL3) δ: 1.2-1.3 (t,3H), 2.9-3.0 (q,2H), 7.45-7.55 (m,2H), 7.8-7.9 (m,4H), 8.02 (s,1H).

Workup

  1. temperaturewas heated
  2. customThe solution was evaporated to dryness
  3. customthe residue was partitioned between water and diethyl ether
  4. washThe organic layer was washed twice with 2M hydrochloric acid
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-974c4dd7ef8e4a03aac8f6e2c3c0618c
Source dataset
uspto-grants-2001_02
Patent number
US06187905B1

Reaction notes

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