Citric Acid → N-(4-methoxy-2-nitro-6-trifluoromethyl-phenyl)-acetamide

HRID 1846513Notes

Reaction equation

HRID 1846513 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([NH:12][C:13](=[O:15])[CH3:14])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[C:19](=O)([O-])[O-:20].[Cs+].[Cs+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:19][O:20][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([NH:12][C:13](=[O:15])[CH3:14])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 10796Cesium carbonateHCID 10778132N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 66978303N-(4-methoxy-2-nitro-6-trifluoromethyl-phenyl)-acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A well stirred mixture of 3.00 g (11.2 mmol) N-(4-fluoro-2-nitro-6-trifluoromethyl-phenyl)-acetamide and 6.00 g (18.4 mmol) caesium carbonate in 90 mL methanol was heated for 10 min at 100° C. in the microwave. After cooling the solvent was eliminated i.vac. and the residue remaining was combined with 100 mL water. The aqueous phase was acidified with 10% citric acid and the product was extracted with 100 mL ethyl acetate. The organic phase was dried and evaporated down i.vac. The residue obtained was purified by flash chromatography. The fractions containing product were combined and evaporated down i.vac.

Workup

  1. temperatureAfter cooling the solvent
  2. extractionthe product was extracted with 100 mL ethyl acetate
  3. customThe organic phase was dried
  4. customevaporated down i.vac
  5. customThe residue obtained
  6. customwas purified by flash chromatography
  7. additionThe fractions containing product
  8. customevaporated down i.vac

Sources & evidence

ORD record
ord-3afb0e9e55ed4e58b2f519c841310936
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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