p-Cyanobenzyl alcohol → N-Hydroxy-4-(hydroxymethyl)benzimidamide

HRID 1665984Notes

Reaction equation

HRID 1665984 reaction equation
Cl.[NH2:2][OH:3].[OH:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.C(=O)([O-])O.[Na+]>CO>[OH:3][N:2]=[C:10]([C:9]1[CH:12]=[CH:13][C:6]([CH2:5][OH:4])=[CH:7][CH:8]=1)[NH2:11]

Participants

5

Reactant 3

HCID 160549p-Cyanobenzyl alcoholHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 53437716N-Hydroxy-4-(hydroxymethyl)benzimidamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of hydroxylamine hydrochloride (5.2 g), 4-(hydroxymethyl)benzonitrile (5.0 g), and sodium hydrogen carbonate (12.6 g) in methanol (50 mL) was heated to reflux for 20 hours. The reaction mixture was filtered through Celite (trade name). Thus, the filtrate was concentrated to thereby give the title compound having the following physical properties. The product was used for next reaction without further purification.

Workup

  1. temperatureto reflux for 20 hours
  2. filtrationThe reaction mixture was filtered through Celite (trade name)
  3. concentrationThus, the filtrate was concentrated

Sources & evidence

ORD record
ord-92c677357d544f8f8e984a06754ebdce
Source dataset
uspto-grants-2011_10
Patent number
US08039674B2

Reaction notes

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