3-nitro-4-(N-ethyl-N-cyclohexylamino)-benzophenone → 3-amino-4-(N-ethyl-N-cyclohexylamino)-benzophenone

HRID 1729649Notes

Reaction equation

HRID 1729649 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N:18]([CH2:25][CH3:26])[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])([O-])=O.[H][H]>C1C=CC=CC=1.C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N:18]([CH2:25][CH3:26])[CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

5

Reactant 2

HCID 233427783-nitro-4-(N-ethyl-N-cyclohexylamino)-benzophenoneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 203412083-amino-4-(N-ethyl-N-cyclohexylamino)-benzophenone

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

7.1 g. of 3-nitro-4-(N-ethyl-N-cyclohexylamino)-benzophenone are dissolved in a 1:1 mixture of benzene and ethyl acetate, and 0.7 g. of palladiumized carbon are added to the mixture. The mixture is hydrogenated at room temperature and 3 atm. hydrogen pressure until the uptake of the calculated amount of hydrogen (this requires about one hour). Thereafter the catalyst is removed by filtration, and the filtrate is evaporated to dryness under reduced pressure. 6.35 g. of crude product are obtained. After recrystallization from isopropanol, 5.8 g. of pure 3-amino-4-(N-ethyl-N-cyclohexylamino)-benzophenone, melting at 106.5°-107.5° C are obtained.

Workup

  1. additionof palladiumized carbon are added to the mixture
  2. customis hydrogenated at room temperature
  3. customthis requires about one hour
  4. customThereafter the catalyst is removed by filtration
  5. customthe filtrate is evaporated to dryness under reduced pressure
  6. customof crude product are obtained
  7. customAfter recrystallization from isopropanol, 5.8 g

Sources & evidence

ORD record
ord-e38883a8eb6a4c1ea60532a3bc7d7dce
Source dataset
uspto-grants-1976_11
Patent number
US03989701

Reaction notes

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