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

HRID 2271454Notes

Reaction equation

HRID 2271454 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-5ac69ad0a03249ffa856d32d010b75f7
Source dataset
uspto-grants-2015_09
Patent number
US09120762B2

Reaction notes

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