Water → HCID 136166982, compound

HRID 1617620Notes

Reaction equation

HRID 1617620 reaction equation
[OH:1][C:2]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=O.Cl.[NH2:25][OH:26].C([O-])(=O)C.[Na+].O>CO>[OH:1][C:2]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3]/[C:4](/[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=[N:25]\[OH:26]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 66668715HCID 66668715, compound

Product 1

HCID 136166982HCID 136166982, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-hydroxy-3,3-diphenyl-1-pyridin-4-yl-propan-1-one (115 mg) in methanol (4 ml) were added hydroxylamine hydrochloride (63 mg) and sodium acetate (75 mg). The mixture was stirred at room temperature for 6 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried using MgSO4, filtered and concentrated to dryness. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 4:1 to 1:3) to give the title compound (60 mg) as a colorless solid, MS (ESI+): m/z=319.1 [M+H]+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 4:1 to 1:3)

Sources & evidence

ORD record
ord-ee79238ca89d47f380c4ddb1aedad479
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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