Hydrochloric Acid → HCID 178468347, compound

HRID 1895208Notes

Reaction equation

HRID 1895208 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1[NH2:4].Cl.[N:14]([O-])=O.[Na+].C([O-])(=O)C.[K+].[C:23]([CH2:26][C:27](=[O:29])[CH3:28])(=[O:25])[CH3:24]>O.CC(O)=O>[F:1][C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:10])([F:11])[F:12])=[CH:5][C:3]=1[NH:4][N:14]=[C:26]([C:27](=[O:29])[CH3:28])[C:23](=[O:25])[CH3:24]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 31261AcetylacetoneHCID 1363492-Fluoro-5-(trifluoromethyl)anilineHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468347HCID 178468347, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2-Fluoro-5-(trifluoromethyl)aniline (2.00 g, 15.6 mmol) was added to a solution of 15.6 mL of HOAc and 2.6 mL of concentrated HCl, stirred, followed by sodium nitrite (0.925 g, 13.4 mmol) in 4 mL of water dropwise at 0° C., and the mixture was stirred at 0° C. for 60 min. Then potassium acetate (3.28 g, 3.5 mmol) and acetylacetone (1.83 mL, 14.5 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 the title compound (2.06 g, 64% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.53 (s, 3H), 2.64 (s, 3H), 7.26-6.30 (m, 1H), 7.39-7.42 (m, 1H), 7.99-8.01 (m, 1H), 14.62 (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-6d0e58f094784b44a6e0fb0aa4d9f903
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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