Ethanol → N-Hydroxy-4-nitrobenzimidamide

HRID 1415128

Reaction equation

HRID 1415128 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH2:13][OH:14].C([O-])([O-])=O.[K+].[K+].C(O)C>O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8](=[N:13][OH:14])[NH2:9])=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 120904-NitrobenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3825473N-Hydroxy-4-nitrobenzimidamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 29.6 g. (0.20 mole) of p-nitrobenzonitrile, 13.9 g. (0.20 mole) of hydroxylamine HCl, 13.8 g. (0.10 mole) of K2CO3 in 700 ml. of ethanol and 70 ml. of water is refluxed for 20 hours, cooled and diluted with 200 ml. of water. After removal of the ethanol by distillation in vacuo, the product is collected by filtration, washed with water and dried to yield 21.6 g. (60%).

Workup

  1. temperaturecooled
  2. additiondiluted with 200 ml
  3. customAfter removal of the ethanol
  4. distillationby distillation in vacuo
  5. filtrationthe product is collected by filtration
  6. washwashed with water
  7. customdried
  8. customto yield 21.6 g

Sources & evidence

ORD record
ord-474104b62e4647feaae5889c7d14df53
Source dataset
uspto-grants-1977_01
Patent number
US04003909

Linked notes

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