Sodium Hydroxide → HCID 85865899, compound

HRID 1296706Notes

Reaction equation

HRID 1296706 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](O)=[CH:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:18][OH:19].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[N:18][OH:19])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 1363756171-(3-Chlorophenyl)-2-(4-pyrimidinyl)ethenol

Product 1

HCID 85865899HCID 85865899, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1-(3-chlorophenyl)-2-(4-pyrimidinyl)ethenol (9.0 g, 38.7 mmol) in methanol (100 mL) was added hydroxylamine hydrochloride (11.5 g, 165 mmol) and sodium hydroxide (60 mL, 2.8 M in water, 166 mmol). The reaction mixture was refluxed 4 hours. After cooling, the excess methanol was removed in vacuo. Ice water (˜300 mL) was added to the resultant mixture and the ice was allowed to melt. The aqueous mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (3:1 to 2:1 hexanes:ethyl acetate) provided 1-(3-chlorophenyl)-2-(4-pyrimidinyl)ethanone oxime (6.5 g, 68%) as a white solid. Rf 0.14 (3:1 hexanes:ethyl acetate): 1H NMR (CDCl3) δ 9.50 (br, 1H), 9.18 (s, 1H), 8.61 (d, 1H), 7.78 (s, 1H), 7.58 (d, 1H), 7.38–7.25 (m, 3H), 4.38 (s, 2H); MS m/z 248 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed 4 hours
  2. temperatureAfter cooling
  3. customthe excess methanol was removed in vacuo
  4. additionIce water (˜300 mL) was added to the resultant mixture
  5. extractionThe aqueous mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-212f12a008c447358cda74e16177f6f8
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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