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

HRID 1698599Notes

Reaction equation

HRID 1698599 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>C(Cl)(Cl)Cl>[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 6212ChloroformSolvent

Procedure

A mixture of methyl 2-amino-4-(trifluoromethyl)benzoate (8.00 g, 0.036 mol), acetic anhydride (11.18 g, 0.109 mol), pyridine (8.62 g, 0.109 mol) and chloroform (20 ml) was stirred at room temperature for 48 h. The reaction mixture was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The extracts were washed with 1N hydrochloric acid and water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with a 50% ethyl acetate/n-hexane to give 8.10 g (0.031 mol 86%) of the title compound as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with 1N hydrochloric acid and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with a 50% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-9dc60f949fc2409899a91ed104cf5d6d
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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