Pyridine → Methyl 2-(acetylamino)-4-(trifluoromethyl)benzoate

HRID 522376Notes

Reaction equation

HRID 522376 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:16](OC(=O)C)(=[O:18])[CH3:17].N1C=CC=CC=1>O1CCOCC1>[C:16]([NH:1][C:2]1[CH:11]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 12601886Methyl 2-Amino-4-(trifluoromethyl)benzoate

Product 1

HCID 11701649Methyl 2-(acetylamino)-4-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the product from Step 1 (5.34 g) in dioxane (25 ml) was added acetic anhydride (6 ml) and pyridine (4 ml). After 60 hours of stirring at 80° C., the solution was concentrated under reduced pressure and the residue was dissolved into ethyl acetate. The organic layer was washed with 2M sodium carbonate, 10% aqueous HCl, water and brine, dried over sodium sulfate and evaporated. The product was purified by flash chromatography (ISCO, 5%-20% ethyl acetate in hexanes) to provide a beige solid (5.27 g). LRMS (ES+) m/z 262.0 (M+H)+.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved into ethyl acetate
  3. washThe organic layer was washed with 2M sodium carbonate, 10% aqueous HCl, water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe product was purified by flash chromatography (ISCO, 5%-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0db450a970824500b61fb2547ef4e1f2
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

Loading…