4-Chloroaniline → 3-Chloropyruvaldehyde 4-chlorophenylhydrazone

HRID 1731415Notes

Reaction equation

HRID 1731415 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N:9]([O-])=O.[Na+].[Cl:13][CH2:14]C(=O)CC(O)=O.[C:21]([O-:24])(=O)[CH3:22].[Na+]>O.Cl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][N:9]=[C:22]([CH2:14][Cl:13])[CH:21]=[O:24])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 119720Butanoic acid, 4-chloro-3-oxo-HCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 886763673-Chloropyruvaldehyde 4-chlorophenylhydrazoneYield 97%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent4×

Conditions

Temperature
0 °C

Procedure

In a mixture of 500 ml of water and 250 ml of concentrated hydrochloric acid is dissolved 128 g of p-chloroaniline. To this solution is added dropwise a solution of 69 g of sodium nitrite in 100 ml of water, while the reaction temperature is maintained at 0° C. Then, to the reaction mixture is added a solution of 136.5 g of 4-chloroacetoacetic acid in 200 ml of water, while the reaction temperature is maintained within the range from 0° C. to 5° C., followed by further addition of a solution of 164 g of sodium acetate in 300 ml of water, whereupon yellow precipitate is produced while bubbling vigorously. The reaction mixture is stirred at a room temperature until the bubbling ceases, followed by collecting the crystals by filtration, washing with water and drying, whereby 224 g of the subject compound is obtained.

Workup

  1. temperaturewhile the reaction temperature is maintained within the range from 0° C. to 5° C.
  2. customis produced
  3. customwhile bubbling vigorously
  4. customby collecting the crystals
  5. filtrationby filtration
  6. washwashing with water
  7. customdrying

Sources & evidence

ORD record
ord-1ffff2bd00264ab29292faecc340d5a2
Source dataset
uspto-grants-1986_11
Patent number
US04621144

Reaction notes

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