Pyridine → HCID 86746404, compound

HRID 1681305Notes

Reaction equation

HRID 1681305 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH:10]([CH3:17])[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.Cl.[NH2:20][OH:21].N1C=CC=CC=1>C(O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[N:20][OH:21])[CH:10]([CH3:17])[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 19805782HCID 19805782, compound

Product 1

HCID 86746404HCID 86746404, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3.6 g of 2',4'-dichloro-2-methyl-2-(3-pyridyl)acetophenone in 15 ml of ethanol and 4 ml of water is treated with 1.4 g of hydroxylamine hydrochloride, 3 ml of pyridine and 90 mg of 4-N,N-dimethylaminopyridine and the reaction mixture is heated to reflux temperature. After 16 hours, it is poured into ice-water and extracted with ethyl acetate. The organic phase is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crystalline crude product is recrystallised from methylene chloride/n-hexane. 2',4'-Dichloro-2-methyl-2-(3-pyridyl)acetophenone oxime is obtained as an E/Z isomer mixture in the form of beige crystals, m.p. 163°-165° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crystalline crude product is recrystallised from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-396b069fbf01407296780782184237e2
Source dataset
uspto-grants-1992_12
Patent number
US05171354

Reaction notes

Loading…