Ethanol → HCID 23062545, compound

HRID 2109393Notes

Reaction equation

HRID 2109393 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[CH2:7][O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:19]=[CH:18][O:17][C:16]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:12]=[CH:13][CH:14]=1)([O-])=O.[Cl-].[NH4+:29].C(O)C>O>[NH2:29][C:25]1[CH:26]=[CH:27][CH:4]=[CH:5][C:6]=1[CH2:7][O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:19]=[CH:18][O:17][C:16]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 23062520HCID 23062520, compound

Product 1

HCID 23062545HCID 23062545, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 3-[3-(3-nitrobenzyloxy)phenyl]-2-furancarboxylate (2.21 g), reduced iron (1.75 g), ammonium chloride (0.67 g), ethanol (30 ml) and water (10 ml) was heated at reflux for 1 hour. After filtering the reaction solution through celite, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/3), thereby giving 1.60 g of ethyl 3-[3-(2-aminobenzyloxy)phenyl)-2-furancarboxylate.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. filtrationAfter filtering the reaction solution through celite
  4. customthe solvent in the filtrate was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-ef18d1de9ff54bc7b5127af481aa6048
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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