Acetic Anhydride → Methyl 2-(acetylamino)-5-nitro-4-(trifluoromethyl)benzoate

HRID 2069261Notes

Reaction equation

HRID 2069261 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH2:17].[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17][C:19](=[O:21])[CH3:20]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 11965778Methyl 2-amino-5-nitro-4-(trifluoromethyl)benzoate

Product 1

HCID 58964493Methyl 2-(acetylamino)-5-nitro-4-(trifluoromethyl)benzoateYield 77%

Procedure

A solution of 2.0 g (7.57 mmol) of 2-amino-5-nitro-4-trifluoromethyl-benzoic acid methyl ester in 20 ml of acetic anhydride is heated to reflux for 4 hours. The mixture is allowed to cool to room temperature and concentrated in vacuo. The residue is taken up in ethyl acetate and washed with water, aqueous saturated NaHCO3-solution and brine. The organic phase is dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, hexane/ethyl acetate 3:1) provided 1.79 g (77%) of 2-acetylamino-5-nitro-4-trifluoromethyl-benzoic acid methyl ester as yellow crystals, m.p. 75-80° C.

Workup

  1. temperatureto reflux for 4 hours
  2. concentrationconcentrated in vacuo
  3. washwashed with water, aqueous saturated NaHCO3-solution and brine
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (SiO2, hexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-ec892883e87347059528338ea07e4fc4
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

Loading…