HCID 57483850, compound → HCID 57483851, compound

HRID 384403Notes

Reaction equation

HRID 384403 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[O:16][C:15]([CH3:17])=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[O:16][C:15]([CH3:17])=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=1

Participants

4

Reactant 1

HCID 57483850HCID 57483850, compound

Product 1

HCID 57483851HCID 57483851, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(2-Methoxy-3-nitro-phenyl)-2-methyl-furan-3-carboxylic acid 53c (450 mg, 1.62 mmol) was dissolved in methanol, followed by addition of 45 mg of palladium on carbon. The reaction mixture was heated to reflux for 4 hours under hydrogen atmosphere. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filtrate was concentrated under reduced pressure to obtain the title compound 5-(2-methoxy-3-amino-phenyl)-2-methyl-furan-3-carboxylic acid 53d (370 mg, yield 92%) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours under hydrogen atmosphere
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-eeb825b794264279b73b812129d62e8e
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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