Pyridine → 3-(Phenylmethyl)-5-isoxazolamine

HRID 1521752Notes

Reaction equation

HRID 1521752 reaction equation
O=[C:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]#[N:5].N1C=CC=CC=1.Cl.[NH2:20][OH:21]>C(O)C.C(OCC)(=O)C.[OH-].[Na+]>[CH2:6]([C:2]1[CH:3]=[C:4]([NH2:5])[O:21][N:20]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 5626663-Oxo-4-phenylbutanenitrile

Product 1

HCID 601742533-(Phenylmethyl)-5-isoxazolamineYield 93%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-oxo-4-phenylbutanenitrile (690 mg, 4.34 mmol) in ethanol (25 mL) is added pyridine (4.91 mL, 60.7 mmol) and hydroxylamine hydrochloride (301 mg, 4.34 mmol). The reaction mixture is allowed to stir at room temperature 84 h. The mixture is diluted with ethyl acetate and 1M aqueous NaOH solution. The layers are separated and the aqueous layer is extracted with ethyl acetate. The organic layers are washed with brine, dried (Na2SO4), and the solvent is removed in vacuo to afford the title compound as a yellow solid (702 mg, 93%). LCMS: 175.20 (M+H+).

Workup

  1. customThe layers are separated
  2. extractionthe aqueous layer is extracted with ethyl acetate
  3. washThe organic layers are washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-442f894bd51843cc9babd786823f232b
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

Loading…