Bis(2-pyridyl) ketone → Di-2-pyridinylmethanone oxime

HRID 963421Notes

Reaction equation

HRID 963421 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=O.Cl.[NH2:16][OH:17]>N1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[N:16][OH:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 88065Bis(2-pyridyl) ketoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 73805Di-2-pyridinylmethanone oximeYield 136.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2 g of di-2-pyridyl-ketone and 1.51 g of hydroxylamine-hydrochloride are added to 13 ml of pyridine and the mixture is held at reflux for 4 hrs. After concentration and cooling there are isolated 2.95 g of crude di-2-pyridyl ketone oxime (contaminated with salts). Addition of 1.18 g of ammonium acetate, 44 ml of dil. ammonia, 30 ml of water and 30 ml of ethanol yields a suspension which is treated portionwise with 4.5 g of zinc powder. The mixture is held at reflux for 4 hrs., cooled and suction filtered. The filtrate is concentrated and the residue is triturated with methanol. 2.54 g of crude C,C-dipyridin-2-yl-methylamine are isolated. Yield: 93%.

Workup

  1. temperatureat reflux for 4 hrs
  2. concentrationAfter concentration
  3. temperaturecooling there

Sources & evidence

ORD record
ord-34628b93ec4e4430a53d5b08914c432a
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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