Water → HCID 131728698, compound

HRID 1364368Notes

Reaction equation

HRID 1364368 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][CH3:16])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[Na+].[ClH:24].[NH2:25]O.O>C(O)C>[ClH:24].[NH2:25][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:18])=[CH:9][CH:10]=1)[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 11334146HCID 11334146, compound

Product 1

HCID 131728698HCID 131728698, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To tert-butyl(4-propionylphenyl)acetate (1 g) in ethanol (20 ml) solution, sodium acetate (0.7 g) and hydroxylamine hydrochloride (0.44 g) were added and the mixture was stirred at 90° C. for 3 hours. Distilled water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over with anhydrous sodium sulfate, then concentrated. Ethanol (22 ml) and 10% palladium carbon (0.6 g) were added to the residue, and the mixture was stirred under hydrogen atmosphere at 5 atm for 40 hours. The insoluble compound was filtered out, then a 4N hydrochloric acid/ethyl acetate solution was added to the filtrate and the mixture concentrated. Hexane/ethyl acetate was added to the residue, and the precipitated solid was collected by filtration to obtain the title compound (0.74 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over with anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additionEthanol (22 ml) and 10% palladium carbon (0.6 g) were added to the residue
  6. stirringthe mixture was stirred under hydrogen atmosphere at 5 atm for 40 hours
  7. filtrationThe insoluble compound was filtered out
  8. additiona 4N hydrochloric acid/ethyl acetate solution was added to the filtrate
  9. concentrationthe mixture concentrated
  10. additionHexane/ethyl acetate was added to the residue
  11. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-87c4f1734a7d44bea993bd81ca532a41
Source dataset
uspto-grants-2011_02
Patent number
US07888348B2

Reaction notes

Loading…