4-chloro-N-cyclohexyl-2-nitroaniline → 4-Chloro-N1-cyclohexylbenzene-1,2-diamine

HRID 861500Notes

Reaction equation

HRID 861500 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[C:4]([N+:15]([O-])=O)[CH:3]=1>C(O)C.[Ni]>[NH2:15][C:4]1[CH:3]=[C:2]([Cl:1])[CH:14]=[CH:13][C:5]=1[NH:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 1

HCID 28372924-chloro-N-cyclohexyl-2-nitroaniline

Product 1

HCID 220971504-Chloro-N1-cyclohexylbenzene-1,2-diamineYield 103.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

41.6 g (0.16 mol) of 4-chloro-N-cyclohexyl-2-nitroaniline were dissolved in 400 ml of ethanol and, after addition of 4.2 g of Raney nickel, hydrogenated under 1 bar at 25° C. The mixture was then filtered and the filtrate was concentrated under reduced pressure to yield 37.3 g (100%) of the product.

Workup

  1. customat 25° C
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4fabd34fa2234d89959fab7bb78f0dc7
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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