Pyridine → 1-(2,4,6-Trichlorophenyl)-2-propanone O-methyloxime

HRID 2170298Notes

Reaction equation

HRID 2170298 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[CH2:10][C:11](=O)[CH3:12].N1C=CC=CC=1.Cl.[CH3:21][O:22][NH2:23]>CO>[CH3:21][O:22][N:23]=[C:11]([CH3:12])[CH2:10][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][C:4]=1[Cl:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 584436631-(2,4,6-Trichlorophenyl)-2-propanone

Product 1

HCID 767875151-(2,4,6-Trichlorophenyl)-2-propanone O-methyloxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of crude 1-(2,4,6-trichloro-phenyl)-propan-2-one prepared as described in example P1, (12 g, 0.050 mol) in methanol (100 ml) was added pyridine (6.8 ml, 0.084 mol), followed by O-methyl-hydroxylamine hydrochloride (6.70 g, 0.080 mol). The resulting mixture was stirred at ambient temperature for 18 hours. Methanol was removed under reduced pressure and the residue poured in 1N hydrochloric acid (300 ml) which was extracted with ethyl acetate (3×100 ml). Organics were combined, washed with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure to give crude 1-(2,4,6-trichloro-phenyl)-propan-2-one O-methyl-oxime E/Z-mixture (12.3 g, 92%), which was taken up for the next reduction step.

Workup

  1. customMethanol was removed under reduced pressure
  2. additionthe residue poured in 1N hydrochloric acid (300 ml) which
  3. extractionwas extracted with ethyl acetate (3×100 ml)
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-753f1a4343174e5aa2c25837139fd6ec
Source dataset
uspto-grants-2015_06
Patent number
US09051272B2

Reaction notes

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