Hydroxyamine hydrochloride → 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oxime

HRID 2409033Notes

Reaction equation

HRID 2409033 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:13]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:12]=[CH:11][C:5]2=[N:6][C:7]=1[C:8](=O)[CH3:9].Cl.[NH2:25][OH:26].CC([O-])=O.[Na+]>CCO>[Cl:1][C:2]1[CH:3]=[C:4]2[N:13]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:12]=[CH:11][C:5]2=[N:6][C:7]=1[C:8](=[N:25][OH:26])[CH3:9]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866898491-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone

Product 1

HCID 1364091001-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oximeYield 102.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone (480 mg, 1.38 mmol), hydroxylamine hydrochloride (478 mg, 6.88 mmol), NaOAc (1.13 g, 13.76 mmol) in EtOH (10 mL) was stirred at RT overnight. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (4:1) to afford 514 mg (94%) of 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oxime as white solid. MS (ESI): m/z=364.0 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was purified by SiO2 chromatography
  4. washeluting with petroleum ether/EtOAc (4:1)

Sources & evidence

ORD record
ord-a1cc9f81ba3b4417b4f29d1682ffd1ad
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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