Acetylacetone → HCID 178468336, compound

HRID 1805555Notes

Reaction equation

HRID 1805555 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[N:13]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[C:22]([CH2:25][C:26](=[O:28])[CH3:27])(=[O:24])[CH3:23]>C(O)(=O)C.Cl.O>[F:1][C:2]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:5][C:3]=1[NH:4][N:13]=[C:25]([C:26](=[O:28])[CH3:27])[C:22](=[O:24])[CH3:23]

Participants

8

Reactant 4

HCID 31261AcetylacetoneHCID 517045Sodium AcetateHCID 27376742-Fluoro-4-(trifluoromethyl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 178468336HCID 178468336, compoundYield 44.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-fluoro-4-(trifluoromethyl)aniline (1.0 g, 5.58 mmol) in 8 mL of acetic acid and 1.3 mL of concentrated hydrochloride solution, sodium nitrite (462 mg, 6.69 mmol) in 2.1 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 (1.37 g, 16.8 mmol, 3.0 equiv.) and acetylacetone (726 mg, 7.26 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 (720 mg, yield 44%): 1H NMR (400 MHz, CDCl3): δ ppm 2.51 (s, 3H), 2.63 (s, 3H), 7.42-7.50 (m, 2H), 7.86 (t, J=8.0 Hz, 1H), 14.56 (s, 1H).

Workup

  1. stirringwas 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-31246f5ef8084cdfbceafd596053c632
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

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