Methanol → methyl 2-[1-(N-allyloxyimino)ethyl]-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate

HRID 4909

Reaction equation

HRID 4909 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[N:16]=2)[C:5]=1[C:6]([O:8][CH3:9])=[O:7])(=O)[CH3:2].Cl.[CH2:26]([O:29][NH2:30])[CH:27]=[CH2:28].C([O-])(=O)C.[K+].CO>O>[CH2:26]([O:29][N:30]=[C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[N:16]=2)[C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH3:2])[CH:27]=[CH2:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 517044Potassium AcetateHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 19089394HCID 19089394, compound

Product 1

HCID 85216991methyl 2-[1-(N-allyloxyimino)ethyl]-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoateYield 46.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g of methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate, 1.0 g of allyloxyamine hydrochloride and 0.9 g of potassium acetate were added to 30 ml of methanol, and were refluxed with stirring for 5 hours. The reaction mixture was then poured into a cold water, and was extracted with ethyl acetate. The organic layer thus formed was washed with firstly dilute hydrochloric acid, then sodium hydrogencarbonate and water in sequence. The organic layer thus washed was then dried and concentrated. The residue oily product was purified by column chromatography to obtain 0.54 g of the aimed compound (melting point=76° to 78° C.) at a yield of 46% as a colorless transparent crystal.

Workup

  1. temperaturewere refluxed
  2. extractionwas extracted with ethyl acetate
  3. customThe organic layer thus formed
  4. washwas washed with firstly dilute hydrochloric acid
  5. washThe organic layer thus washed
  6. customwas then dried
  7. concentrationconcentrated
  8. customThe residue oily product was purified by column chromatography

Sources & evidence

ORD record
ord-f731ed3622dd4070b9453e090fd140d9
Source dataset
uspto-grants-1993_09
Patent number
US05242895

Linked notes

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