Potassium Carbonate → N-Hydroxy-4-nitrobenzimidamide

HRID 75812

Reaction equation

HRID 75812 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:8][OH:9].[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1)([O-:12])=[O:11]>CCOC(C)=O>[OH:9][N:8]=[C:17]([NH2:18])[C:16]1[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120904-NitrobenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3825473N-Hydroxy-4-nitrobenzimidamideYield 86.88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate and hydroxylamine hydrochloride were added to an ethanolic solution of 4-nitrobenzonitrile. The solution was refluxed at 80° C. for 5 hours. After completion of the reaction the solvent was evaporated and the crude so obtained was dissolved in EtOAc and washed with water, brine, then dried by sodium sulfate and concentrated to give a solid. It was the purified by column chromatography and further recrystallized from EtOAc: petroleum ether to obtain the title product in 86.88% yield. 1H NMR (DMSO-d6) δ: 6.071 (s, 2H, NH2) 8.24 (d, 2H, CH), 8.317 (d, 2H, CH), 10.138 (S, 1H, OH), ms (m/z) 180 (M−−H).

Workup

  1. customAfter completion of the reaction the solvent
  2. customwas evaporated
  3. customthe crude so obtained
  4. washwashed with water, brine
  5. dry with materialdried by sodium sulfate
  6. concentrationconcentrated
  7. customto give a solid
  8. custompurified by column chromatography
  9. customfurther recrystallized from EtOAc

Sources & evidence

ORD record
ord-7fd2556d99c845808d545772b2cd8c05
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

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