2,4-Difluoroaniline → HCID 178468346, compound

HRID 2089866Notes

Reaction equation

HRID 2089866 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[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[CH:8]=[C:7]([F:9])[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 97092,4-DifluoroanilineHCID 31261AcetylacetoneHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468346HCID 178468346, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,4-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) 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 (550 mg, 30% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.48 (s, 3H), 2.61 (s, 3H), 6.91-7.00 (m, 2H), 7.70-7.76 (m, 1H), 14.72 (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-24968a93721a4b18b2f48af63efa4b2b
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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