p-Cyanobenzyl alcohol → N'-Hydroxy-4-(hydroxymethyl)benzene-1-carboximidamide

HRID 1941874Notes

Reaction equation

HRID 1941874 reaction equation
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.Cl.[NH2:12][OH:13].C([O-])(O)=O.[Na+]>CO>[OH:13][N:12]=[C:7]([NH2:8])[C:6]1[CH:9]=[CH:10][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

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

Product 1

HCID 53437716N'-Hydroxy-4-(hydroxymethyl)benzene-1-carboximidamideYield 101.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 4-(hydroxymethyl)benzonitrile (22.43 g, 0.1685 g), hydroxylamine hydrochloride (18.67 g, 0.2689 mol) and NaHCO3 (45.22 g, 0.538 mol) in methanol (250 mL) was heated to reflux overnight. Upon cooling, the heterogeneous mixture was filtered and the solids were washed with additional methanol. The filtrate was evaporated to dryness to afford an off-white solid. The solids were suspended in ˜75 mL hot methanol, then cooled to room temperature and filtered. The filtrate was evaporated to afford N′-hydroxy-4-(hydroxymethyl)benzimidamide (28.5 g) as a white solid. The material was used without further purification. The compound had an HPLC retention time=0.232 min. −Column: CHROMOLITH® SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.2% H3PO4; Solvent B=90% MeOH, 10% H2O, 0.2% H3PO4. LC/MS M+1=167.3

Workup

  1. temperatureto reflux overnight
  2. temperatureUpon cooling
  3. filtrationthe heterogeneous mixture was filtered
  4. washthe solids were washed with additional methanol
  5. customThe filtrate was evaporated to dryness
  6. customto afford an off-white solid
  7. filtrationfiltered
  8. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a3bfb01f27d442ed8e07de3525291c7d
Source dataset
uspto-grants-2013_03
Patent number
US08389509B2

Reaction notes

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