Hydrochloric Acid → HCID 178468360, compound

HRID 1805562Notes

Reaction equation

HRID 1805562 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH2:4].Cl.[N:11]([O-])=O.[Na+].C([O-])(=O)C.[K+].[C:20]([CH2:23][C:24](=[O:26])[CH3:25])(=[O:22])[CH3:21]>O.CC(O)=O>[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH:4][N:11]=[C:23]([C:24](=[O:26])[CH3:25])[C:20](=[O:22])[CH3:21]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 31261AcetylacetoneHCID 677752,5-DifluoroanilineHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468360HCID 178468360, compoundYield 107.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2,5-Difluoroaniline (2.10 g, 15.5 mmol) was added to a solution of 21.6 mL of HOAc and 3.6 mL of concentrated HCl, stirred, followed by sodium nitrite (1.28 g, 18.6 mmol) in 6 mL of water dropwise at 0° C., and the mixture was stirred at 0° C. for 60 min. Then potassium acetate (4.56 g, 46.5 mmol) and acetylacetone (2.07 mL, 20.15 mmol) were added dropwise. The mixture was stirred at room temperature overnight, filtered. The precipitate was dissolved in CH2Cl2, washed with water, dried over Na2SO4 and concentrated under reduced pressure to give a crude product (4.00 g, 67% yield), which was used directly to the next step: 1H NMR (400 MHz, CDCl3): δ ppm 2.51 (s, 3H), 2.62 (s, 3H), 6.79-6.83 (m, 1H), 7.09-7.15 (m, 1H), 7.43-7.47 (m, 1H), 14.57 (s, 1H)

Workup

  1. stirringthe mixture was stirred at 0° C. for 60 min
  2. stirringThe mixture was stirred at room temperature overnight
  3. filtrationfiltered
  4. dissolutionThe precipitate was dissolved in CH2Cl2
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0b71972261b46689cb399880fb99556
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

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