Pyridine → (E)-1-[3-(4-Chlorophenoxy)phenyl]buten-3-one oxime

HRID 704814

Reaction equation

HRID 704814 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:8]=[C:9](/[CH:13]=[CH:14]/[C:15](=O)[CH3:16])[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22].N1C=CC=CC=1>CO.CCOCC>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:8]=[C:9](/[CH:13]=[CH:14]/[C:15](=[N:21][OH:22])[CH3:16])[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 20073366(E)-1-[3-(4-Chlorophenoxy)phenyl]buten-3-one

Product 1

HCID 86744553(E)-1-[3-(4-Chlorophenoxy)phenyl]buten-3-one oximeYield 101.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The product from step (a) (19 g) and hydroxylamine hydrochloride (6.9 g) were taken up in methanol (100 ml), pyridine (20 ml) was added and the mixture stirred for 1 hour. The mixture was then stripped, redissolved in ether (200 ml), washed with 2 N aqu. HCl and satd. aqu. NaCl, dried over MgSO4, and stripped to give the desired product (20.3 g).

Workup

  1. washwashed with 2 N aqu
  2. dry with materialNaCl, dried over MgSO4

Sources & evidence

ORD record
ord-8ac384bb3aa048a7a33174f8bc9c7ce6
Source dataset
uspto-grants-1991_01
Patent number
US04988733

Linked notes

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