Sodium Hydroxide → 2-(4-Chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone oxime

HRID 723999Notes

Reaction equation

HRID 723999 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=O)[CH:3]=1.Cl.[NH2:20][OH:21].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:20][OH:21])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 218740542-(4-Chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone

Product 1

HCID 738517522-(4-Chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone in methanol (200 mL) was added hydroxylamine hydrochloride (27.2 g, 392 mmol) followed by the addition of a sodium hydroxide solution (15.7 g, 392 mmol in 50 mL of water). The resulting suspension was heated at reflux for 1 hour and then allowed to cool to room temperature. The mixture was concentrated and water was added to the resulting slurry. A white precipitate formed, which was collected by filtration, washed with water and dried to give 2-(4-chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone oxime (11.8 g) as a white solid. 1H NMR (CDCl3): δ 8.47 (d, 1H), 7.72 (d, 2H), 7.36 (d, 1H), 7.19 (dd, 1H), 6.91 (d, 2H), 4.43 (s, 2H), 3.84 (s, 3H); MS m/z 277 (M+1).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 1 hour
  3. concentrationThe mixture was concentrated
  4. additionwater was added to the resulting slurry
  5. customA white precipitate formed
  6. filtrationwhich was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-73afd8b72a61464fac6e9b9983891338
Source dataset
uspto-grants-2006_11
Patent number
US07141569B2

Reaction notes

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