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

HRID 2271449Notes

Reaction equation

HRID 2271449 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 19a (400 mg, 1.45 mmol) was dissolved in 30 mL of ethyl acetate followed by addition of 100 mg of palladium on carbon (10%) and ammonium formate (360 mg, 5.8 mmol). The mixture was heated to reflux for 3 hours. The mixture was filtered and concentrated under reduced pressure to obtain the title compound 4-(3-amino-2-methoxy-phenyl)-thiophene-2-carboxylic acid 19b (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. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12bc1dc9004f4378be580b83e75829dd
Source dataset
uspto-grants-2015_09
Patent number
US09120762B2

Reaction notes

Loading…