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

HRID 384328Notes

Reaction equation

HRID 384328 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[S: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[S: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 574838125-(2-Methoxy-3-nitro-phenyl)thiophene-2-carboxylic acid

Product 1

HCID 574838135-(3-Amino-2-methoxy-phenyl)-thiophene-2-carboxylic acidYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(2-methoxy-3-nitro-phenyl)thiophene-2-carboxylic acid 12a (7.7 g, 27.6 mmol) was dissolved in 300 mL of ethyl acetate followed by addition of 500 mg of palladium on carbon and ammonium formate (6.96 g, 110 mmol). The reaction mixture was heated to reflux for 4 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)-thiophene-2-carboxylic acid 12b (6.2 g, yield 90.1%) as a grey solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 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-baaf46089a5c48ceb860ce49207ff558
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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