1-[5-(4-Nitro-phenyl)-furan-2-yl]-ethanone → HCID 2302841, compound

HRID 1579611Notes

Reaction equation

HRID 1579611 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15]([CH3:17])=[O:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O>[Ni].C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15]([CH3:17])=[O:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 44054061-[5-(4-Nitro-phenyl)-furan-2-yl]-ethanone

Product 1

HCID 2302841HCID 2302841, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 58 g (0.25 mole) of methyl 5-(p-nitrophenyl)-2-furyl ketone, 2 tsp. of Raney Ni and 750 ml of ethanol was shaken under hydrogen pressure for one hour with the theoretical amount of H2 being absorbed. An additional 2000 ml of ethanol was added to the reaction mixture. The mixture was heated to reflux and the catalyst was removed by filtration. The filtrate was treated with ethereal HCl and the resulting solid was filtered and air-dried to yield 41 g (8.15%) of methyl 5-(p-aminophenyl)-2-furyl ketone. An analytical sample was prepared by drying a sample at room temperature in the vacuum pistol, m.p. scinters above 160°.

Workup

  1. customabsorbed
  2. additionAn additional 2000 ml of ethanol was added to the reaction mixture
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. customthe catalyst was removed by filtration
  6. additionThe filtrate was treated with ethereal HCl
  7. filtrationthe resulting solid was filtered
  8. customair-dried

Sources & evidence

ORD record
ord-b1f74e838cd24402931dc1631eb560d6
Source dataset
uspto-grants-1976_01
Patent number
US03931247

Reaction notes

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