Water → HCID 136460478, compound

HRID 1755990Notes

Reaction equation

HRID 1755990 reaction equation
[C:1]([C:4]1[N:9]=[C:8]([O:10][CH2:11][CH3:12])[CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+].O>C(O)C>[C:1](=[N:14]/[OH:15])(\[C:4]1[N:9]=[C:8]([O:10][CH2:11][CH3:12])[CH:7]=[CH:6][N:5]=1)/[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 19392519HCID 19392519, compound

Product 1

HCID 136460478HCID 136460478, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-acetyl-4-ethoxypyrimidine (1.8 g), hydroxylamine hydrochloride (0.83 g) and sodium acetate (2.2 g) in a mixture of ethanol:water (30:10 ml) was heated under reflux for 3 hours. The reaction mixture was then poured into water and extracted with ethyl acetate (×3). the combined extracts were washed with brine, dried and concentrated to give a solid which was washed with hexane to give (E)-2-acetyl-4-ethoxypyrimidine oxime as an off-white solid (1.15 g, 60% yield); 1H NMR (270 MHz): δ1.44(3H,t), 2.38(3H,s), 4.50(2H,q), 6.68(1H,d), 8.48(1H,d), 9.80(1H,brs) ppm.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionextracted with ethyl acetate (×3)
  3. washthe combined extracts were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give a solid which
  7. washwas washed with hexane

Sources & evidence

ORD record
ord-ea4e77370e674725bbad888aacadc907
Source dataset
uspto-grants-1995_08
Patent number
US05439910

Reaction notes

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