HCID 57483854, compound → HCID 57483855, compound

HRID 384407Notes

Reaction equation

HRID 384407 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[C:11]=2[O:19][CH3:20])=[CH:8][CH:9]=1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[C:11]=2[O:19][CH3:20])=[CH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 57483854HCID 57483854, compound

Product 1

HCID 57483855HCID 57483855, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(2-Methoxy-3-nitro-phenyl)-furan-2-carboxylic acid methyl ester 54a (500 mg, 1.8 mmol) was dissolved in methanol followed by addition of 50 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 concentrated under reduced pressure. The resulting residue was recrystallized from a solvent mixture of ethyl acetate/n-hexane (V:V=1:5) and dried to obtain the title compound 5-(3-amino-2-methoxy-phenyl)-furan-2-carboxylic acid methyl ester 54b (370 mg, yield 83%) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours under hydrogen atmosphere
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customThe resulting residue was recrystallized from a solvent mixture of ethyl acetate/n-hexane (V:V=1:5)
  5. customdried

Sources & evidence

ORD record
ord-39185a268e56420980d2b76b8d866cbb
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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