5-(4-Nitro-phenyl)-furan-2-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide → 5-(4-Amino-phenyl)-furan-2-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide

HRID 2108691Notes

Reaction equation

HRID 2108691 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([C:12]1[O:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2>[Pd].C(O)C>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([NH:9][C:10]([C:12]1[O:13][C:14]([C:17]3[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2

Participants

4

Reactant 1

HCID 48400265-(4-Nitro-phenyl)-furan-2-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide

Product 1

HCID 181804805-(4-Amino-phenyl)-furan-2-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-(4-nitro-phenyl)-furan-2-carboxylic acid(1-aza-bicyclo[2.2.2]oct-3-yl)-amide (5.0 g, 14.6 mmol), palladium on carbon (0.5 g, 10%) and ethanol (250 ml) was stirred under hydrogen atmosphere for 2 hours. The palladium was filtered off on celite. The crude mixture was purified by silica gel chromatography, using a mixture of dichloromethane:methanol (9:1) and 1% methanol as eluent. Yield 2.5 g (55%). M.p. 103-113° C.

Workup

  1. filtrationThe palladium was filtered off on celite
  2. customThe crude mixture was purified by silica gel chromatography
  3. additiona mixture of dichloromethane:methanol (9:1) and 1% methanol as eluent

Sources & evidence

ORD record
ord-da96244970cb41d2b48bffce0583ed9a
Source dataset
uspto-grants-2009_04
Patent number
US07514450B2

Reaction notes

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