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

HRID 384319Notes

Reaction equation

HRID 384319 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 9a (4.23 g, 16.09 mmol) was dissolved in 125 mL of ethyl acetate followed by addition of 423 mg of palladium on carbon and ammonium formate (4.054 g, 64.35 mmol). The reaction mixture was heated to reflux for 3.5 hours. The reaction was monitored by TLC until the disappearance of the starting materials. 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 9b (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-3784f771f3d44424b389f90281317888
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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