Water → HCID 136388387, compound

HRID 393150Notes

Reaction equation

HRID 393150 reaction equation
[CH:1]([C:3]1[C:8]([CH:9]([N:13]([CH3:23])[C:14](=[O:22])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]([CH3:12])[CH3:11])=[CH:7][N:6]=[CH:5][N:4]=1)=O.Cl.[NH2:25][OH:26].C([O-])(=O)C.[K+].O>CO>[OH:26][N:25]=[CH:1][C:3]1[C:8]([CH:9]([N:13]([CH3:23])[C:14](=[O:22])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]([CH3:12])[CH3:11])=[CH:7][N:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium AcetateHCID 12151357HCID 12151357, compound

Product 1

HCID 136388387HCID 136388387, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.0 g (3.2 mmol) of N-(1-(4-formylpyrimidin-5-yl)-2-methylpropyl]-N-methylphenylacetamide was dissolved in 30 ml of methanol, and 0.45 g (6.5 mmol) of hydroxylamine hydrochloride and 0.63 g (6.4 mmol) of potassium acetate were added and reacted at room temperature for 1 hour. After completion of the reaction, the product was poured into water and extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydrogencarbonate solution, an aqueous citric acid solution, water and an aqueous sodium chloride solution, in this order, dried and concentrated, and the obtained oily product was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate) to obtain 0.45 g (yield: 43%) of N-[1-(4-hydroxyiminomethylpyrimidin-5-yl)-2-methylpropyl]-N-methylphenylacetamide as colorless crystals (melting point: 171-172° C.).

Workup

  1. customreacted at room temperature for 1 hour
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous sodium hydrogencarbonate solution
  5. dry with materialan aqueous citric acid solution, water and an aqueous sodium chloride solution, in this order, dried
  6. concentrationconcentrated
  7. customthe obtained oily product was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-725d65171c4a440e835b27249e5a3d91
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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