Hydroxylamine → 4-[Amino(hydroxyimino)methyl]benzamide

HRID 614634Notes

Reaction equation

HRID 614634 reaction equation
Cl.[NH2:2][OH:3].[Na].N[OH:6].[C:7](#[N:16])[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1>C(O)C>[C:7](=[N:2][OH:3])([NH2:16])[C:8]1[CH:15]=[CH:14][C:11]([C:12]([NH2:13])=[O:6])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 121721,4-DicyanobenzeneHCID 443297Hydroxyamine hydrochlorideHCID 5360545Sodium

Product 1

HCID 737809844-[Amino(hydroxyimino)methyl]benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent4×

Procedure

A solution of 7 g hydroxylamine hydrochloride (0.10 mol) was dissolved in 15 ml of ethanol and cooled to 0°-5° C. To the mixture was added 2.3 g sodium (0.10 mol) dissolved in 30 ml ethanol. After generating the free hydroxylamine, 3.05 g of terephthalonitrile (23.8 mmol) suspended in 40 ml of ethanol was added dropwise to the ethanol solution. The mixture was then refluxed for 20 hours. The volume of solution was reduced to 5 ml, and upon cooling a precipitate formed which was filtered. The yield was 2.21 g (48%), m.p. 224-225° C (decomp.). The infrared spectrum (KBr pellet) showed formation of peaks at 2.91 μ and 2.98 μ (NH2), 306 μ (OH), and 6.07 and 6.26 μ (C=N).

Workup

  1. temperaturecooled to 0°-5° C
  2. temperatureThe mixture was then refluxed for 20 hours
  3. temperatureupon cooling a precipitate
  4. customformed which
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-7b75cc70b7e440d08352a553dbe2bb23
Source dataset
uspto-grants-1979_03
Patent number
US04145524

Reaction notes

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