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

HRID 384396Notes

Reaction equation

HRID 384396 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])[S: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])[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 574838444-(3-Nitro-2-methoxy-phenyl)-thiophene-2-carboxylic acid

Product 1

HCID 574838454-(3-Amino-2-methoxy-phenyl)-thiophene-2-carboxylic acidYield 113.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(3-Nitro-2-methoxy-phenyl)-thiophene-2-carboxylic acid 51a (400 mg, 1.45 mmol) was dissolved in 30 mL of ethyl acetate followed by addition of 100 mg of palladium on carbon and ammonium formate (360 mg, 5.8 mmol). The 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 and concentrated under reduced pressure to obtain the title compound 4-(3-amino-2-methoxy-phenyl)-thiophene-2-carboxylic acid 51b (410 mg) as a brown oil, which was directly used in the next step.

Workup

  1. temperatureThe 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-3bd127ef4e814f87bbc1e40309555619
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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