Ammonia → HCID 22345641, compound

HRID 584323Notes

Reaction equation

HRID 584323 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:13]=1[CH3:21].N>C(O)C.O.C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:18][C:16]1[CH:15]=[CH:14][C:13]([CH3:21])=[C:12]([C:3]2[CH:4]=[CH:5][C:6]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:7][C:2]=2[CH3:1])[CH:17]=1

Participants

8

Reactant 2

HCID 222AmmoniaHCID 223456091-(2,2′-Dimethyl-5′-nitro[1,1′-biphenyl]-4-yl)-1-propanone

Product 1

HCID 22345641HCID 22345641, compound

Reagents, catalysts & solvents 5

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.2 g (7.8 mmol) of 1-(2,2′-dimethyl-5′-nitrobiphenyl-4-yl)-1-propanone are dissolved in a mixture of 80 ml of ethanol and 40 ml of water and 10 ml of acetic acid. The mixture is refluxed while 1.7 g (31 mmol) of iron powder are added. The medium is heated for 1 hour and then treated by addition of aqueous ammonia, cooled and filtered through Celite. The solution obtained is diluted in ethyl acetate and then washed with water, and the organic phase is dried and concentrated under reduced pressure. After chromatography on a column of silica (eluent: 60 heptane/40 ethyl acetate), a yellow oil is obtained (m=1.9 g; Y=96%).

Workup

  1. additionare added
  2. temperatureThe medium is heated for 1 hour
  3. temperaturecooled
  4. filtrationfiltered through Celite
  5. customThe solution obtained
  6. washwashed with water
  7. customthe organic phase is dried
  8. concentrationconcentrated under reduced pressure
  9. customAfter chromatography on a column of silica (eluent: 60 heptane/40 ethyl acetate), a yellow oil is obtained (m=1.9 g; Y=96%)

Sources & evidence

ORD record
ord-98a213965bad4c418850b16f3652c242
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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