Ammonium formate → HCID 59615657, compound

HRID 384418Notes

Reaction equation

HRID 384418 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])[NH: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])[NH:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 596156634-(3-nitro-2-methoxy-phenyl)-1H-pyrrole-2-carboxylic acid

Product 1

HCID 59615657HCID 59615657, compoundYield 23.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(3-Nitro-2-methoxy-phenyl)-1H-pyrrole-2-carboxylic acid 57g (633 mg, 2.41 mmol) was dissolved in 15 mL of ethyl acetate followed by addition of 127 mg of palladium on carbon and ammonium formate (609 mg, 9.66 mmol). Upon completion of the addition, the reaction mixture was heated to reflux for 2 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered to remove palladium on carbon and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 4-(3-amino-2-methoxy-phenyl)-1H-pyrrole-2-carboxylic acid 57h (130 mg, yield 23.2%) as a grey solid.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 2 hours
  4. filtrationThe mixture was filtered
  5. customto remove palladium on carbon
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7dabd57e5fb343d8bf03bf458cf32828
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

Loading…