Water → 4-bromo-N'-hydroxy-3-methylbenzenecarboximidamide

HRID 1721318Notes

Reaction equation

HRID 1721318 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].Cl.[NH2:12][OH:13].CC(C)([O-])C.[K+].O>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[NH:7])[NH:12][OH:13])=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 27374944-Bromo-3-methylbenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 1784266494-bromo-N'-hydroxy-3-methylbenzenecarboximidamideYield 309.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-bromo-3-methylbenzonitrile (20.0 g) in methanol (100 ml) was treated with hydroxylamine hydrochloride (4×2.08 g) and potassium t-butoxide (4×3.25 g) over 6 hours and the resulting mixture heated at reflux for 18 h. After cooling, the reaction mixture was poured into water (800 ml), the suspension stirred for 30 min, and the white solid filtered off and dried in vacuo to give the title compound (21.2 g).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 18 h
  3. temperatureAfter cooling
  4. filtrationthe white solid filtered off
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e38c2cbda5d244fa9eebc13fa3bf44f9
Source dataset
uspto-grants-1996_04
Patent number
US05510350

Reaction notes

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