Sodium Hydroxide → 2-(6-Chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone oxime

HRID 1373401

Reaction equation

HRID 1373401 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=O)[CH:5]=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].[OH-].[Na+]>CO>[Cl:1][C:2]1[N:7]=[C:6]([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:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 219922342-(6-Chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone

Product 1

HCID 738583202-(6-Chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone oximeYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(6-chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone (37.4 g, 142.9 mmol) in methanol (500 mL) was added hydroxylamine hydrochloride (49.7 g, 714.5 mmol) followed by the addition of a sodium hydroxide solution (28.6 g, 714.5 mmol in 50 mL of water). The resulting suspension was heated at reflux for 2 hours 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-(6-chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone oxime (38.7 g, 97%) as a white solid. 1H NMR (CDCl3): δ 8.23 (b, 1H), 7.63 (d, 2H), 7.48 (d, 1H), 7.12 (m, 2H), 6.83 (dd, 2H), 4.33 (s, 2H), 3.76 (s, 3H); MS m/z 277 (M+1).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 2 hours
  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-26ab8e6603c8417982d8d206653c395b
Source dataset
uspto-grants-2007_01
Patent number
US07160897B2

Linked notes

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