Acetylacetone → HCID 178468338, compound

HRID 1624679Notes

Reaction equation

HRID 1624679 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[N:10]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[C:19]([CH2:22][C:23](=[O:25])[CH3:24])(=[O:21])[CH3:20]>C(O)(=O)C.Cl.O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][N:10]=[C:22]([C:23](=[O:25])[CH3:24])[C:19](=[O:21])[CH3:20])=[C:4]([F:9])[CH:3]=1

Participants

8

Reactant 4

HCID 31261AcetylacetoneHCID 938984-Chloro-2-fluoroanilineHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468338HCID 178468338, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-chloro-2-fluoroaniline (1 g, 6.87 mmol) in 9.8 mL of acetic acid and 1.6 mL of concentrated hydrochloride solution, sodium nitrite (568 mg, 8.24 mmol) in 2.6 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 were added sodium acetate (1.69 g, 20.6 mmol) and acetylacetone (893 mg, 8.93 mmol). The mixture was stirred at room temperature for 2 h, filtered, washed with water, EtOH/H2O (1/1) and hexane, and dried to give the title compound (1 g, 57% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.49 (s, 3H), 2.60 (s, 3H), 7.15-7.25 (m, 2H), 7.69 (t, J=8.4 Hz, 1H), 14.64 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-9d008b7e5d394bc09f5da6c9b7d1b413
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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