2,4,6-Trimethoxybenzonitrile → N-HYDROXY-2,4,6-TRIMETHOXY-BENZAMIDINE

HRID 1734572Notes

Reaction equation

HRID 1734572 reaction equation
Cl.[NH2:2][OH:3].CC[O-].[Na+].[Na].[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[C:12]=1[C:13]#[N:14]>C(O)C>[CH3:22][O:21][C:15]1[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:11]([O:10][CH3:9])[C:12]=1[C:13](=[N:2][OH:3])[NH2:14]

Participants

6

Reactant 4

HCID 757312,4,6-TrimethoxybenzonitrileHCID 443297Hydroxyamine hydrochlorideHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 5191888N-HYDROXY-2,4,6-TRIMETHOXY-BENZAMIDINE

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 13.8 g of hydroxylamine hydrochloride in 100 ml of ethanol is added, at a temperature in the region of 15° C., a solution of NaOC2H5 prepared by dissolving 4.3 g of sodium in 100 ml of ethanol. 12 g of 2,4,6-trimethoxybenzonitrile are introduced into the medium, followed by heating at reflux for 41 h before evaporating to dryness. The crystals are washed with water and with dichloromethane.

Workup

  1. additionis added, at a temperature in the region of 15° C.
  2. temperatureby heating
  3. temperatureat reflux for 41 h
  4. custombefore evaporating to dryness
  5. washThe crystals are washed with water and with dichloromethane

Sources & evidence

ORD record
ord-6d38f2833779447cbd4d3dbb4de43b23
Source dataset
uspto-grants-1996_07
Patent number
US05534530

Reaction notes

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