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

HRID 384385Notes

Reaction equation

HRID 384385 reaction equation
[N+:1]([C:4]1[C:5]([O:19][CH3:20])=[C:6]([C:11]2[O:15][C:14]([C:16]([OH:18])=[O:17])=[CH:13][CH:12]=2)[CH:7]=[C:8]([CH3:10])[CH:9]=1)([O-])=O.C([O-])=O.[NH4+]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[C:5]([O:19][CH3:20])=[C:6]([C:11]2[O:15][C:14]([C:16]([OH:18])=[O:17])=[CH:13][CH:12]=2)[CH:7]=[C:8]([CH3:10])[CH:9]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57483835HCID 57483835, compound

Product 1

HCID 574838365-(3-Amino-2-methoxy-5-methyl-phenyl)-furan-2-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(3-Nitro-2-methoxy-5-methyl-phenyl)-furan-2-carboxylic acid 46a (410 mg, 1.48 mmol) was dissolved in 28 mL of ethyl acetate followed by addition of 61 mg of palladium on carbon and ammonium formate (658 mg, 10.44 mmol). Upon completion of the addition, the reaction mixture was heated to reflux for 3 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered to remove palladium on carbon. The filtrate was concentrated under reduced pressure and dried to obtain the title compound 5-(3-amino-2-methoxy-5-methyl-phenyl)-furan-2-carboxylic acid 46b (356 mg, yield 97.3%) as a white solid.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 3 hours
  4. filtrationThe mixture was filtered
  5. customto remove palladium on carbon
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customdried

Sources & evidence

ORD record
ord-98dedb1088a84e12a0513f0cfb4ab830
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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