Ammonium formate → 5-(3-Amino-2-methoxy-phenyl)-furan-2-carboxylic acid

HRID 238705Notes

Reaction equation

HRID 238705 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[O:16][C:15]([C:17]([OH:19])=[O:18])=[CH:14][CH:13]=1.C([O-])=O.[NH4+]>C(OCC)(=O)C.[Pd]>[NH2:9][C:8]1[C:3]([O:2][CH3:1])=[C:4]([C:12]2[O:16][C:15]([C:17]([OH:19])=[O:18])=[CH:14][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 574838035-(2-Methoxy-3-nitro-phenyl)furan-2-carboxylic acid

Product 1

HCID 574838045-(3-Amino-2-methoxy-phenyl)-furan-2-carboxylic acidYield 74.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(2-methoxy-3-nitro-phenyl)furan-2-carboxylic acid 4e (4.23 g, 16.09 mmol) was dissolved in 125 mL of ethyl acetate followed by addition of 423 mg of palladium on carbon (10%) and ammonium formate (4.054 g, 64.35 mmol). The reaction mixture was heated to reflux for 3.5 hours. The mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound 5-(3-amino-2-methoxy-phenyl)-furan-2-carboxylic acid 4f (2.79 g, yield 74.4%) as a light green solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3.5 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f266b7b1db174df685f7fe7a514a1caa
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Reaction notes

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