3-Fluoroaniline → HCID 178468333, compound

HRID 1624537Notes

Reaction equation

HRID 1624537 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[N:9]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[C:18]([CH2:21][C:22](=[O:24])[CH3:23])(=[O:20])[CH3:19]>O.Cl.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:5][N:9]=[C:21]([C:22](=[O:24])[CH3:23])[C:18](=[O:20])[CH3:19])[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 97423-FluoroanilineHCID 31261AcetylacetoneHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468333HCID 178468333, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-fluoroaniline (1000 mg, 9.00 mmol) in 5 mL of water and 5 mL of concentrated hydrochloride solution, sodium nitrite (746 mg, 10.80 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 (2220 mg, 27.00 mmol) and acetylacetone (990 mg, 9.90 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-[(3-fluorophenyl)hydrazono]pentane-2,4-dione (650 mg, 33%).

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-077d65706c524bdf939b7852196bea34
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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