Acetylacetone → HCID 178468364, compound

HRID 1407201Notes

Reaction equation

HRID 1407201 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[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>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH:4][N:10]=[C:22]([C:23](=[O:25])[CH3:24])[C:19](=[O:21])[CH3:20]

Participants

8

Reactant 4

HCID 31261AcetylacetoneHCID 796472,6-DifluoroanilineHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468364HCID 178468364, compoundYield 21.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,6-difluoroaniline (1.0 g, 7.75 mmol) in 11.1 mL of acetic acid and 1.69 mL of concentrated hydrochloride solution, sodium nitrite (600 mg, 9.3 mmol) in 2.7 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 (1.78 g, 21.7 mmol) and acetylacetone (1 g, 10 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 (400 mg, 21% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.43 (s, 3H), 2.61 (s, 3H), 6.97-7.03 (m, 2H), 7.05-7.15 (m, 1H), 14.42 (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-4358b9ecfe674d23a7e027cda0f9581f
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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