Sodium Hydroxide → 2-(4-Bromopyridin-2-yl)-1-(4-methoxyphenyl)ethanone oxime

HRID 705375Notes

Reaction equation

HRID 705375 reaction equation
[Br: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.O>[Br: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

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 682760292-(4-Bromopyridin-2-yl)-1-(4-methoxyphenyl)ethanone

Product 1

HCID 885407812-(4-Bromopyridin-2-yl)-1-(4-methoxyphenyl)ethanone oximeYield 84.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of Example 19A (13.41 g, 43.8 mmol) in methanol (231 mL) was added hydroxylamine hydrochloride (15.22 g, 219 mmol) to give a thick slurry. The mixture was treated with a solution of sodium hydroxide (8.76 g, 219 mmol) in water (58 mL), heated at reflux for two hours, cooled and concentrated to a paste. The paste was treated with 100-150 mL of water and stirred for 15 minutes to give a solid that was collected by filtration, washed with water and dried to constant mass to give the title compound as a powder (11.86 g, 84%). MS (ESI+) m/z 321/323 (M+H)+.

Workup

  1. customto give a thick slurry
  2. temperatureheated
  3. temperatureat reflux for two hours
  4. temperaturecooled
  5. concentrationconcentrated to a paste
  6. additionThe paste was treated with 100-150 mL of water
  7. customto give a solid
  8. filtrationthat was collected by filtration
  9. washwashed with water
  10. customdried to constant mass

Sources & evidence

ORD record
ord-306566ad99db43508cbc868f42098211
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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