Acetylacetone → HCID 178468331, compound

HRID 2089859Notes

Reaction equation

HRID 2089859 reaction equation
[F:1][C:2]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][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[C:8]([C:9]([F:10])([F:11])[F:12])=[CH:7][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 1455693-Amino-2-fluorobenzotrifluorideHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468331HCID 178468331, compoundYield 55.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-fluoro-3-(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) and acetylacetone (726 mg, 7.26 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 (900 mg, 55% yield). 1H NMR (400 MHz, CDCl3): δ ppm 2.51 (s, 3H), 2.63 (s, 3H), 7.30-7.34 (m, 1H), 7.38-7.41 (m, 1H), 7.94-7.96 (m, 1H), 14.66 (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-fcac86469f34486ba1fc94b090bfd51e
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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