Hydroxyamine hydrochloride → HCID 86697891, compound

HRID 338075Notes

Reaction equation

HRID 338075 reaction equation
[CH2:1]([N:4]([CH2:15][CH:16]=[CH2:17])[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=O)[CH:2]=[CH2:3].C([O-])(=O)C.[Na+].Cl.[NH2:24][OH:25]>C(O)C>[CH2:1]([N:4]([CH2:15][CH:16]=[CH2:17])[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=[N:24][OH:25])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86697890HCID 86697890, compound

Product 1

HCID 86697891HCID 86697891, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

2-(Diallylamino)-1-(4-fluorophenyl)ethanone (13.38 g, 57.36 mmol) is dissolved in ethanol (250 mL) and sodium acetate (5.7 g) is added followed by hydroxylamine hydrochloride (5.23 g, 74.6 mmol). The reaction is warmed to 70° C. for 2.5 hours then stirred at room temperature for 16 hours. The mixture is concentrated and the resulting residue is purified by silica gel flash chromatography eluting with ethyl acetate/hexanes (gradient 0-100%). The isolated material is repurified a second time to give the title compound (7.76 g, 54.5%). ES/MS (m/e): 249 (M+H).

Workup

  1. concentrationThe mixture is concentrated
  2. customthe resulting residue is purified by silica gel flash chromatography
  3. washeluting with ethyl acetate/hexanes (gradient 0-100%)
  4. customThe isolated material is repurified a second time

Sources & evidence

ORD record
ord-3fff75d69942449eb55a4e6d869bea48
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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