Hydroxyamine hydrochloride → N'-hydroxy-3-(hydroxymethyl)benzimidamide

HRID 2242245Notes

Reaction equation

HRID 2242245 reaction equation
Cl.[OH:2][NH2:3].C(=O)(O)[O-].[Na+].[OH:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15]>CO>[OH:2][N:3]=[C:14]([C:13]1[CH:16]=[CH:17][CH:18]=[C:11]([CH2:10][OH:9])[CH:12]=1)[NH2:15]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 27346773-(Hydroxymethyl)benzonitrile

Product 1

HCID 74865044N'-hydroxy-3-(hydroxymethyl)benzimidamideYield 105.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxyl amine hydrochloride (2.29 g, 32.9 mmol) and sodium bicarbonate (5.52 g, 65.8 mmol) were added to 3-(hydroxymethyl)benzonitrile (2.19 g, 16.4 mmol) and methanol (30 mL) and stirred at reflux for 18 hours. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo to give the title compound (2.88 g, 100% yield) as a solid.

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-50dca5ceb82844329cd1beb4a8475d8a
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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