HCID 86657769, compound → HCID 58443674, compound

HRID 2381270Notes

Reaction equation

HRID 2381270 reaction equation
[CH3:1][O:2][N:3]=[CH:4][CH2:5][CH2:6][C:7]1[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=1[Cl:15]>C(O)(=O)C.[BH3-]C#N.[Na+]>[CH3:1][O:2][NH:3][CH2:4][CH2:5][CH2:6][C:7]1[C:8]([Cl:15])=[CH:9][C:10]([Cl:14])=[CH:11][C:12]=1[Cl:13]

Participants

4

Reactant 1

HCID 86657769HCID 86657769, compound

Product 1

HCID 58443674HCID 58443674, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 5003444Sodium cyanoborohydrideSolvent

Procedure

To a stirred solution of 3-(2,4,6-trichloro-phenyl)-propionaldehyde O-methyl-oxime in acetic acid, NaCNBH3 was added at 0° C.-10° C. The reaction mass was then stirred at ambient temperature for 6 hours. When the TLC confirmed completion of the reaction, acetic acid was removed by azeotropic distillation. The residue was basified with 10% NaOH solution and aqueous solution was extracted with ethyl acetate (3×30 ml). The combined organic layer was washed with water and brine. The organic layer was then dried over anhydrous sodium sulphate and concentrated under reduced pressure. The resulting crude mass was purified over column chromatography (silica gel 60-120 mesh, 3% ethyl acetate in hexane) to afford O-methyl-N-[3-(2,4,6-trichloro-phenyl)-propyl]-hydroxylamine (0.4 g, 88%).

Workup

  1. customwas removed by azeotropic distillation
  2. extractionwas extracted with ethyl acetate (3×30 ml)
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialThe organic layer was then dried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude mass was purified over column chromatography (silica gel 60-120 mesh, 3% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-44dd9f37281747a787bdd22237d14d5f
Source dataset
uspto-grants-2012_09
Patent number
US08258169B2

Reaction notes

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