Methyl 3-nitro-5-(trifluoromethyl)benzoate → methyl 3-amino-5-(trifluoromethyl)benzoate

HRID 534838Notes

Reaction equation

HRID 534838 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 18942157Methyl 3-nitro-5-(trifluoromethyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 4026781methyl 3-amino-5-(trifluoromethyl)benzoateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl 3-nitro-5-(trifluoromethyl)benzoate (Reference Example 27, 24.6 g, 98.9 mmol) in ethanol (1500 mL) was sparged in a Parr bottle with nitrogen for 10 min. After this time, 10 wt % Pd/C (5.0 g, 5.0 mmol) was added and the reaction mixture was subjected to 40 psi of hydrogen on Parr shaker at room temperature for 1 h. After this time, the reaction mixture was filtered through a pad of celite and concentrated under reduced pressure to provide Methyl 3-amino-5-(trifluoromethyl)benzoate (20.6 g, 95%) as a light purple oil.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bfd73034a81045d2bc73a579878aec5f
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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