Chloroform → HCID 18923365, compound

HRID 1899984Notes

Reaction equation

HRID 1899984 reaction equation
[CH2:1]([N:8](C)[C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([CH:16]=[O:17])=[C:11]([Cl:18])[CH:10]=1)C1C=CC=CC=1.C(Cl)(Cl)Cl>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[Cl:15][C:13]1[CH:14]=[C:9]([CH:10]=[C:11]([Cl:18])[C:12]=1[CH:16]=[O:17])[NH:8][CH3:1]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 18923653HCID 18923653, compound

Product 1

HCID 18923365HCID 18923365, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-benzyl-3,5-dichloro-4-formyl-N-methylaniline (820 mg) in ethyl acetate (10 ml) was added palladium hydroxide (80 mg) under nitrogen atmosphere. This mixture was stirred under hydrogen atmosphere under atmospheric pressure at ambient temperature for one and half an hour. The precipitate was dissolved into chloroform and filtered through celite and the filtrate was concentrated in vacuo. The residual solid was suspended in diisopropyl ether and warmed at 90° C. After being stirred and cooled, the solid was collected by filtration to afford 3,5-dichloro-4-formyl-N-methylaniline (470 mg) as a pale brown solid.

Workup

  1. filtrationfiltered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. temperaturewarmed at 90° C
  4. stirringAfter being stirred
  5. temperaturecooled
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-e1d76a7fa75e491b83c5a7ab53b11974
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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