Hydrochloric Acid → Methyl 2-amino-3-nitro-4-(trifluoromethyl)benzoate

HRID 1698601Notes

Reaction equation

HRID 1698601 reaction equation
C([NH:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=O)C.Cl>CO>[NH2:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([C:18]([F:19])([F:20])[F:21])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67272857Methyl 2-(acetylamino)-3-nitro-4-(trifluoromethyl)benzoate

Product 1

HCID 67272484Methyl 2-amino-3-nitro-4-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of methyl 2-(acetylamino)-3-nitro-4-(trifluoromethyl)benzoate (1.00 g, 3.27 mmol) and 10% hydrochloric acid in methanol solution (10 ml) was heated at 55° C. for 16 h. The reaction mixture was concentrated in vacuo. The residue was diluted with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with a 30% ethyl acetate/n-hexane to give 780 mg (0.030 mol 90%) of the title compound as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with aqueous saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with 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 30% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-e52db10c80dd437798113264bed85c83
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

Loading…