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

HRID 1742618Notes

Reaction equation

HRID 1742618 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-92bd12bb3e974777b13f1992b6e62366
Source dataset
uspto-grants-1994_08
Patent number
US05340810

Reaction notes

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