Hydroxylamine → HCID 178510829, compound

HRID 884122Notes

Reaction equation

HRID 884122 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]#[N:23])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)=[O:6].[OH2:28].[NH2:29]O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22](=[NH:29])[NH:23][OH:28])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)=[O:6]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 962WaterHCID 11430Potassium CarbonateHCID 68527071HCID 68527071, compound

Product 1

HCID 178510829HCID 178510829, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3,4-dichloro-N-[6-(4-cyanomethylphenoxy)pyridin-3-yl]benzamide (700 mg, 1.76 mmol) in ethanol (30 mL) were added water (2 mL), hydroxylamine (420 mg, 12.71 mmol) and potassium carbonate (1.76 g, 12.73 mmol). Under argon, the resulting solution was stirred under reflux for 4 hours. The resulting reaction solution was concentrated under reduced pressure. To the residue was added water, and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, evaporated, and the residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1), to thereby yield 510 mg of the title compound.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe resulting reaction solution
  3. concentrationwas concentrated under reduced pressure
  4. additionTo the residue was added water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-4bf3391dfcf046f280897359aa365134
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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