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

HRID 384343Notes

Reaction equation

HRID 384343 reaction equation
[N+:1]([C:4]1[C:5]([O:19][CH3:20])=[C:6]([C:11]2[S: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[S: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 574838195-(3-Nitro-2-methoxy-5-methyl-phenyl)thiophene-2-carboxylic acid

Product 1

HCID 574838205-(3-Amino-2-methoxy-5-methyl-phenyl)-thiophene-2-carboxylic acidYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(3-Nitro-2-methoxy-5-methyl-phenyl)thiophene-2-carboxylic acid 24b (0.29 g, 1 mmol) was dissolved in 30 mL of ethyl acetate followed by addition of 0.06 g of palladium on carbon and ammonium formate (0.25 g, 4 mmol). Upon completion of the addition, the reaction mixture was heated to reflux for 45 minutes. 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)-thiophene-2-carboxylic acid 24c (0.26 g, yield 99%) as a green solid.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 45 minutes
  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-a254bd0597f545d9b97182b93769115d
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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