bis(4-nitrophenyl)methanone → n-hydroxy-1,1-bis(4-nitrophenyl)methanimine

HRID 1417892Notes

Reaction equation

HRID 1417892 reaction equation
Cl.[NH2:2][OH:3].[N+:4]([C:7]1[CH:23]=[CH:22][C:10]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=O)=[CH:9][CH:8]=1)([O-:6])=[O:5]>C(O)C>[N+:4]([C:7]1[CH:23]=[CH:22][C:10]([C:11](=[N:2][OH:3])[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)([O-:6])=[O:5]

Participants

4

Reactant 2

HCID 245528bis(4-nitrophenyl)methanoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 289708n-hydroxy-1,1-bis(4-nitrophenyl)methanimineYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of hydroxylamine hydrochloride (10.2 g, 147 mmol) was added to a suspension of 4,4'-dinitrobenzophenone (19 g, 70 mmol) in 100 ml of ethanol. The reaction mixture was heated to reflux for 2 hours, cooled to room temperature, and the solid collected by filtration. Recrystallization from ethanol provided the title compound (14.0 g, 70%) as pale yellow crystals. mp 194° C.; 1H NMR (D6 -DMSO) 12.25 (s, 1H), 8.35 (d, 2H), 8.20 (d, 2H), 7.60 (d, 4H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationthe solid collected by filtration
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-0c06d09921f44d06a2f48746524169a7
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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