Hydroxyamine hydrochloride → Methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-hydroxyiminomethylbenzoate

HRID 4905Notes

Reaction equation

HRID 4905 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=O)[C:13]=2[C:14]([O:16][CH3:17])=[O:15])[N:4]=1.Cl.[OH:25][NH2:26].C([O-])(=O)C.[K+]>CO>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[N:26][OH:25])[C:13]=2[C:14]([O:16][CH3:17])=[O:15])[N:6]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium AcetateHCID 14678388Methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-formylbenzoate

Product 1

HCID 86747184Methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-hydroxyiminomethylbenzoateYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.0 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-formylbenzoate, 0.8 g of hydroxyamine hydrochloride, 1.1 g of potassium acetate and 10 ml of methanol were placed in a 50 ml eggplant type flask, and were stirred for 10 minutes at room temperature. Methanol was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The organic layer was washed with water, 5% hydrochloric acid and a saturated salt aqueous solution, and was dried with magnesium sulfate anhydride. After filtering, a small amount of Florisil was added to the resultant product, and was stirred for 5 minutes. The Florisil was filtered out, and ethyl acetate was distilled off under reduced pressure to obtain 1.5 g of the aimed compound (refractive index=1.5558) at a yield of 72%.

Workup

  1. distillationMethanol was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with water, 5% hydrochloric acid
  4. dry with materiala saturated salt aqueous solution, and was dried with magnesium sulfate anhydride
  5. filtrationAfter filtering
  6. additiona small amount of Florisil was added to the resultant product
  7. stirringwas stirred for 5 minutes
  8. filtrationThe Florisil was filtered out
  9. distillationethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e77e497ab65949148fe18d9b14c87ef9
Source dataset
uspto-grants-1993_09
Patent number
US05242895

Reaction notes

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