Ethyl Acetate → HCID 58043585, compound

HRID 1618010Notes

Reaction equation

HRID 1618010 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:29][OH:30].C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[CH2:9]/[C:10](/[C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[N:29]\[OH:30])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 66668567HCID 66668567, compound

Product 1

HCID 58043585HCID 58043585, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-(3-(4-bromophenyl)-3-(2,4-difluorophenyl)propanoyl)-1-methyl-pyridin-2(1H)-one (0.2 g, 463 μmol) in ethanol (5 mL) and water (0.2 mL) was added hydroxylamine hydrochloride (80.4 mg, 1.16 mmol) and sodium hydrogencarbonate (77.7 mg, 925 μmol) and the resulting colourless suspension was heated at reflux (100° C. oil bath temperature) for 4.5 hours. After cooling down the reaction mixture was poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system eluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100). Colourless foam (0.205 g, 99%). MS (ESI+): m/z=449.1 ([M+H]+).

Workup

  1. temperaturethe resulting colourless suspension was heated
  2. temperatureAfter cooling down the reaction mixture
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washThe organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. additiontreated with silica gel
  9. customevaporated
  10. customThe compound was purified by silica gel chromatography on a 20 g column
  11. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100)

Sources & evidence

ORD record
ord-824049f3a413410e936ed9c2e4328ec8
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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