4-Chloroaniline → HCID 178468337, compound

HRID 2089728Notes

Reaction equation

HRID 2089728 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+].C([O-])(=O)C.[Na+].[C:18]([CH2:21][C:22](=[O:24])[CH3:23])(=[O:20])[CH3:19]>C(O)(=O)C.Cl.O.C(O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][N:9]=[C:21]([C:22](=[O:24])[CH3:23])[C:18](=[O:20])[CH3:19])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 78124-ChloroanilineHCID 31261AcetylacetoneHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468337HCID 178468337, compoundYield 90%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-chloroaniline (1000 mg, 7.87 mmol) in 10 mL of acetic acid and 2 mL of concentrated hydrochloride solution, sodium nitrite (652 mg, 9.45 mmol) in 4 mL of water was added dropwise at 0° C., and the mixture was stirred at 0° C. for 1 h. Then to the reaction mixture was added dropwise a solution of sodium acetate (1936 mg, 23.61 mmol) and acetylacetone (1023 mg, 10.23 mmol) in 10 mL of ethanol and 6 mL of water. The mixture was stirred at room temperature overnight, filtered, washed with water, EtOH/H2O (1:1) and hexane, and dried to give 3-[(4-chlorophenyl)hydrazono]pentane-2,4-dione (1680 mg, 90%).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. filtrationfiltered
  3. washwashed with water, EtOH/H2O (1:1) and hexane
  4. customdried

Sources & evidence

ORD record
ord-84255124cd9e4e25b37568662df3418f
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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