1-[1-(Isopropylthio)ethyl]-2-nitrobenzene → 2-[1-(Isopropylthio)ethyl]aniline

HRID 1176012Notes

Reaction equation

HRID 1176012 reaction equation
[CH:1]([S:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)[CH3:6])([CH3:3])[CH3:2].[H][H]>C(O)C.[Ni]>[CH:1]([S:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 574980151-[1-(Isopropylthio)ethyl]-2-nitrobenzeneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 574980162-[1-(Isopropylthio)ethyl]anilineYield 87.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

44 g (0.188 mol) 1-[1-(isopropylthio)ethyl]-2-nitrobenzene (VII-1) are dissolved in 250 ml ethanol, mixed with 3 g Raney nickel and hydrogenated in the autoclave for 6 hours at room temperature with 3 bar of hydrogen. After 6 hours another 3 g Raney nickel are added and hydrogenation is continued for another 16 hours at room temperature with 3 bar hydrogen. The catalyst is then removed by filtration and the solvent removed under vacuum. The crude product is purified by column chromatography (silica gel, 3:1 hexane/methyl t-butyl ether). 32 g (97.3% purity by HPLC, 84.4% theoretical yield) of 2-[1-(isopropylthio)ethyl]aniline are obtained as a yellow oil [logP (pH 2.3)=2.45].

Workup

  1. customThe catalyst is then removed by filtration
  2. customthe solvent removed under vacuum
  3. customThe crude product is purified by column chromatography (silica gel, 3:1 hexane/methyl t-butyl ether)

Sources & evidence

ORD record
ord-0095de273bdc466eb92f63e88a043a39
Source dataset
uspto-grants-2010_11
Patent number
US07842710B2

Reaction notes

Loading…