Hydroxyamine hydrochloride → HCID 86697891, compound

HRID 470203Notes

Reaction equation

HRID 470203 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-bf41574318b94c9096ea4609efc86490
Source dataset
uspto-grants-2014_01
Patent number
US08629270B2

Reaction notes

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