{4-[Bis(2-methylpropyl)amino]-3-nitrophenyl}(phenyl)methanone → 3-amino-4-(N,N-diisobutylamino)-benzophenone

HRID 1729648Notes

Reaction equation

HRID 1729648 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N:18]([CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:19][CH:20]([CH3:22])[CH3:21])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])([O-])=O.[H][H]>[Ni].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N:18]([CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:19][CH:20]([CH3:21])[CH3:22])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

5

Reactant 2

HCID 23342780{4-[Bis(2-methylpropyl)amino]-3-nitrophenyl}(phenyl)methanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 203412043-amino-4-(N,N-diisobutylamino)-benzophenone

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10.63 g. of 3-nitro-4-(N,N-diisobutylamino)-benzophenone are dissolved in 106 ml. of ethyl acetate, the solution is poured into a hydrogenating apparatus, and 5,3 g. of Raney-nickel are added. The reaction mixture is hydrogenated at room temperature and atmospheric pressure until the uptake of the calculated amount of hydrogen (this requires generally about 1.5 hours). Thereafter the catalyst is removed by filtration and the clear solution is evaporated to dryness under reduced pressure. The obtained 9.4 g. of solid are recrystallized from isopropanol, to yield pure 3-amino-4-(N,N-diisobutylamino)-benzophenone; m.p.: 59°-60° C.

Workup

  1. customis hydrogenated at room temperature
  2. customThereafter the catalyst is removed by filtration
  3. customthe clear solution is evaporated to dryness under reduced pressure
  4. customof solid are recrystallized from isopropanol

Sources & evidence

ORD record
ord-eacb5e2ceda84ddaa9314cc74b6dff05
Source dataset
uspto-grants-1976_11
Patent number
US03989701

Reaction notes

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