Stannous Chloride → methyl 3-amino-5-(trifluoromethyl)benzoate

HRID 355368Notes

Reaction equation

HRID 355368 reaction equation
[Sn](Cl)Cl.[N+:4]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])([O-])=O>C(O)C>[NH2:4][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 18942157Methyl 3-nitro-5-(trifluoromethyl)benzoate

Product 1

HCID 4026781methyl 3-amino-5-(trifluoromethyl)benzoateYield 56.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Tin (II) chloride (60 g) was added to a solution of methyl 3-nitro-5-(trifluoromethyl)benzoate (25 g, 100 mmol) in ethanol (600 ml) and the mixture was heated to 60° C. for 2 hours. The mixture was cooled and concentrated under reduced pressure to approximately one third volume. The mixture was added slowly to saturated aqueous sodium hydrogen carbonate (1000 ml) and the resulting mixture was filtered through celite. The filter cake was washed with ethyl acetate (500 ml). The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure to give methyl 3-amino-5-(trifluoromethyl)benzoate as an orange solid (12.4 g), 1H NMR (360 MHz,CDCl3) δ 3.95 (3H, s), 7.08 (1H, br s), 7.51 (1H, s), and 7.66 (1H, s).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under reduced pressure to approximately one third volume
  3. additionThe mixture was added slowly to saturated aqueous sodium hydrogen carbonate (1000 ml)
  4. filtrationthe resulting mixture was filtered through celite
  5. washThe filter cake was washed with ethyl acetate (500 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0f6c6afc452a428e8393c6ce38f31fd0
Source dataset
uspto-grants-1998_11
Patent number
US05830892

Reaction notes

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