Ammonium formate → Methyl 2,3-diamino-4-(trifluoromethyl)benzoate

HRID 1698602Notes

Reaction equation

HRID 1698602 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]([C:15]([F:16])([F:17])[F:18])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67272484Methyl 2-amino-3-nitro-4-(trifluoromethyl)benzoate

Product 1

HCID 67273073Methyl 2,3-diamino-4-(trifluoromethyl)benzoateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirring solution of methyl 2-amino-3-nitro-4-(trifluoromethyl)benzoate (5.80 g, 0.022 mol), ammonium formate (30.0 g, 0.476 mol) in ethanol (300 ml) was added 10% palladium on carbon (500 mg) at room temperature and stirred for 2 h. Insoluble was filtered off and filtrates were concentrated in vacuo. The residue was diluted with water 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 20% ethyl acetate/n-hexane to give 5.10 g (0.022 mol, 99%) of the title compound as a yellow powder.

Workup

  1. filtrationInsoluble was filtered off
  2. concentrationfiltrates were concentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel with a 20% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-5c4a8b6ecd3e4743af42d5f4fd53f7fa
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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