Acetylacetone → HCID 178468334, compound

HRID 1624672Notes

Reaction equation

HRID 1624672 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][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[C:8]([F:9])=[CH:7][CH:6]=[CH:5][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 782782,3-DifluoroanilineHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468334HCID 178468334, compoundYield 48.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,3-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 was added dropwise a mixture of sodium acetate (1.78 g, 21.7 mmol, 3.0 equiv.) and acetylacetone (1 g, 10 mmol, 1.3 equiv.). 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 (900 mg, 48% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.49 (s, 3H), 2.61 (s, 3H), 6.93-7.00 (m, 1H), 7.11-7.17 (m, 1H), 7.50-7.56 (m, 1H), 14.64 (s, 1H).

Workup

  1. additionThen to the reaction mixture was added dropwise
  2. stirringThe mixture was stirred at room temperature for 2 h
  3. filtrationfiltered
  4. washwashed with water, EtOH/H2O (1/1) and hexane
  5. customdried

Sources & evidence

ORD record
ord-9decb61241394c6fb29188dc73cd5f12
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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