HCID 538490, compound → Acetoacetanilide

HRID 1756874Notes

Reaction equation

HRID 1756874 reaction equation
Cl[C:2](Cl)([C:12]([CH3:14])=[O:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[H][H]>O.C1(C)C=CC=CC=1.[H][H]>[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:4])[CH2:2][C:12]([CH3:14])=[O:13]

Participants

6

Reactant 2

HCID 538490HCID 538490, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 7592Acetoacetanilide

Reagents, catalysts & solvents 3

HCID 178418361HCID 178418361, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2.46 g (0.01 mole) of α,α-dichloroacetoacetanilide was dissolved in 20 ml of water and 30 ml of toluene, and dehalogenated with hydrogen using 5% Pd/C as catalyst. Hydrogen was allowed to react until no more would be absorbed. The first equivalent (251 ml at 739 mm pressure and 25° C.) was absorbed in 50 minutes (a rate of about 5 ml/min) whereas the 274 ml (second equivalent) was absorbed at the much slower rate of about 0.9 ml/min. On the basis of the hydrogen absorbed, it was concluded that the dehalogenation had proceeded to remove both chlorines and hence to give acetoacetanilide. This was confirmed by filtering off the catalyst, separating off the water phase and finally isolating the product from the toluene. Obtained were 1.57 g or 89% of acetoacetanilide, mp 79°-84° C.

Workup

  1. customto react until no more
  2. customwould be absorbed
  3. customThe first equivalent (251 ml at 739 mm pressure and 25° C.) was absorbed in 50 minutes (a rate of about 5 ml/min) whereas the 274 ml (second equivalent)
  4. customwas absorbed at the much slower rate of about 0.9 ml/min
  5. customOn the basis of the hydrogen absorbed
  6. customto remove both chlorines

Sources & evidence

ORD record
ord-00df3c290120427eb1a7a9cffe7c2c5b
Source dataset
uspto-grants-1995_08
Patent number
US05442115

Reaction notes

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