Hydroxyamine hydrochloride → HCID 89704741, compound

HRID 1481338Notes

Reaction equation

HRID 1481338 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([Cl:15])[C:9]=1[CH:16]=O)(=[O:3])[CH3:2].CC([O-])=O.[Na+].Cl.[NH2:24][OH:25]>CN(C=O)C>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([Cl:15])[C:9]=1[CH:16]=[N:24][OH:25])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 89704896HCID 89704896, compound

Product 1

HCID 89704741HCID 89704741, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(3,5-dichloro-2-formylphenoxy)ethyl acetate (1.48 mmol) in 2.5 mL DMF was cooled to 0° C. and NaOAc (1.62 mmol) followed by hydroxylamine HCl (1.62 mmol) were added. The ice bath was removed and the reaction mixture was stirred at RT for 1.5 h. The mixture was diluted with EtOAc and washed once with water and brine. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using Hept and EtOAc gives the desired compound as white solid.

Workup

  1. additionwere added
  2. customThe ice bath was removed
  3. additionThe mixture was diluted with EtOAc
  4. washwashed once with water and brine
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification with CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-5ebac6574fb04ab1b7afb99350068586
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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