Hydroxylamine → HCID 53396275, compound

HRID 1640883Notes

Reaction equation

HRID 1640883 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[NH2:11][OH:12].O>C(O)(=O)C.O1CCOCC1.C(Cl)(Cl)Cl.C(O)(C)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[N:11][OH:12])[CH3:9])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-one

Product 1

HCID 53396275HCID 53396275, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Conditions

Temperature
150 °C

Procedure

Combine 1-(6-chloropyridin-3-yl)ethanone (3.4 g, 22.8 mmol), hydroxylamine (50%) in water (5.77 g, 87.4 mmol) and 0.75 mL of acetic acid in 15 mL of dioxane in a pressure vessel. Seal the vessel and heat the mixture in an oil bath for 3 h at 150° C. Cool the mixture to RT. Dilute with chloroform/IPA (3/1), wash with water, and aqueous saturated sodium chloride. Separate the layers and dry the organic layer over sodium sulfate. Concentrate in vacuo to afford the title compound (3.52 g, 94%). MS (ES) m/z 171 [M+1]+.

Workup

  1. customSeal the vessel
  2. temperatureCool the mixture to RT
  3. washwash with water, and aqueous saturated sodium chloride
  4. customSeparate the layers
  5. dry with materialdry the organic layer over sodium sulfate
  6. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-f8fc75ea881242f49d7b4f0ec095152f
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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