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

HRID 391411Notes

Reaction equation

HRID 391411 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>CO.[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

4

Reactant 1

HCID 18942157Methyl 3-nitro-5-(trifluoromethyl)benzoate

Product 1

HCID 4026781methyl 3-amino-5-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 3-nitro-5-(trifluoromethyl)benzoate (9.0 g, 36.1 mmol) in methanol (30 mL) was flushed with nitrogen, and treated with palladium (10% on charcoal, 0.90 g). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Flash chromatography on silica gel (30% ethyl acetate/hexanes) afforded 6.8 g (86%). 1H-NMR (CDCl3, 500 MHz) δ 7.64 (s, H), 7.49 (s, 1H), 7.05 (s, 1H), 3.91 (s, 3H). Mass spec.: 220.05 (MH)+.

Workup

  1. customThe flask was flushed with hydrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customFlash chromatography on silica gel (30% ethyl acetate/hexanes) afforded 6.8 g (86%)

Sources & evidence

ORD record
ord-1250c5e0644c464faa02b47fb5be7ef2
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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