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

HRID 243821Notes

Reaction equation

HRID 243821 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-6fc5d554ea6a4ccb8735b339b659b6ee
Source dataset
uspto-grants-2014_02
Patent number
US08653305B2

Reaction notes

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