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

HRID 1395014Notes

Reaction equation

HRID 1395014 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-b256b11487f74bf4afd57570a982f31a
Source dataset
uspto-grants-1980_05
Patent number
US04201723

Reaction notes

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