Hydroxyamine hydrochloride → N-[5-(hydroxyiminomethyl)-indan-1-yl] propionic acid amide

HRID 2063502Notes

Reaction equation

HRID 2063502 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[CH2:7][CH2:6]2)=O.Cl.[OH:18][NH2:19].C([O-])(=O)C.[Na+]>C(O)C.O>[OH:18][N:19]=[CH:1][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86653805N-(5-formylindan-1-yl)propionic acid amide

Product 1

HCID 86653806N-[5-(hydroxyiminomethyl)-indan-1-yl] propionic acid amideYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.18 g of N-(5-formylindan-1-yl)propionic acid amide were suspended in 20 ml of ethanol and 10 ml of water. 0.57 g of hydroxyamine hydrochloride and 0.67 g of sodium acetate were added to this suspension followed by stirring overnight at room temperature. The reaction liquid was concentrated under reduced pressure followed by pouring into ice water and extracting with ethyl acetate. After washing the organic layer with saturated aqueous sodium bicarbonate and saturated brine, the organic layer was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.25 g of the target compound. Yield: 100%

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. additionby pouring into ice water
  4. extractionextracting with ethyl acetate
  5. washAfter washing the organic layer with saturated aqueous sodium bicarbonate and saturated brine
  6. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-acd48f1bdc514a3d9bda762b57260d32
Source dataset
uspto-grants-2012_10
Patent number
US08288393B2

Reaction notes

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