Hydroxyamine hydrochloride → HCID 54474526, compound

HRID 1741038Notes

Reaction equation

HRID 1741038 reaction equation
CC(C)([O-])C.[K+].Cl.[NH2:8][OH:9].[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[CH3:19]>CO>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15](=[N:8][OH:9])[NH2:16])=[CH:13][C:12]=1[CH3:19]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 27374944-Bromo-3-methylbenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 54474526HCID 54474526, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methanol (20 ml) at 5° C. was treated portionwise over 5 min. with stirring with potassium t-butoxide (1.68 g, 0.015 mole), then after a further 5 mins the solution was treated with hydroxylamine hydrochloride (1.11 g, 0.016 mole). The resulting mixture was allowed to warm to room temperature, stirred for 1 h, then treated with a solution of 4-bromo-3-methylbenzonitrile (2.0 g, 0.010 mole) in methanol (10 ml) and heated under reflux for 3 h. The mixture was allowed to cool, then filtered through kieselguhr and the filtrate concentrated in vacuo to afford the title compound as a white solid (1.56 g, 100%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. temperatureto cool
  4. filtrationfiltered through kieselguhr
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-af8e8429723b45efb30fabd33e134700
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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