Ammonium formate → 4-(3-Amino-2-methoxy-phenyl)-furan-2-carboxylic acid

HRID 238720Notes

Reaction equation

HRID 238720 reaction equation
[N+:1]([C:4]1[C:5]([O:18][CH3:19])=[C:6]([C:10]2[CH:11]=[C:12]([C:15]([OH:17])=[O:16])[O:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.C([O-])=O.[NH4+]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[C:5]([O:18][CH3:19])=[C:6]([C:10]2[CH:11]=[C:12]([C:15]([OH:17])=[O:16])[O:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 574838244-(3-Nitro-2-methoxy-phenyl)-furan-2-carboxylic acid

Product 1

HCID 574838254-(3-Amino-2-methoxy-phenyl)-furan-2-carboxylic acidYield 73.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(3-nitro-2-methoxy-phenyl)-furan-2-carboxylic acid 22c (500 mg, 1.9 mmol) was dissolved in 15 mL of ethyl acetate followed by addition of 100 mg of palladium on carbon and ammonium formate (429 mg, 7.6 mmol). The reaction mixture was heated to reflux for 3 hours. The mixture was filtered to remove palladium on carbon and concentrated under reduced pressure to obtain the title compound 4-(3-amino-2-methoxy-phenyl)-furan-2-carboxylic acid 22d (325 mg, yield 73.4%) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe mixture was filtered
  4. customto remove palladium on carbon
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e44d30add4846908f96a26eaa1b24ba
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Reaction notes

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