[2-(2-Chloro-4-nitrophenyl)ethyl]diethylamine → 3-Chloro-4-(2-diethylaminoethyl)phenylamine

HRID 1820864Notes

Reaction equation

HRID 1820864 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15]>C1COCC1.[H][H].[Ni]>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15]

Participants

5

Reactant 1

HCID 68816908[2-(2-Chloro-4-nitrophenyl)ethyl]diethylamine

Product 1

HCID 596916173-Chloro-4-(2-diethylaminoethyl)phenylamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 178418361HCID 178418361, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2.00 g (7.79 mmol) of [2-(2-chloro-4-nitrophenyl)ethyl]diethylamine (VI.1.c) is dissolved in 50 mL of THF and hydrogenated for 2.5 hours at ambient temperature at a pressure of 25 psi with hydrogen and 0.8 g of Raney nickel as catalyst. Then the catalyst is filtered off and the solvent is eliminated. Yield: 1.80 g (100% of theory); Rf value: 0.45 (Alox, petroleum ether/ethyl acetate=1:1); C12H19ClN2; EII mass spectrum: m/z=227/229 [M+H]+.

Workup

  1. filtrationThen the catalyst is filtered off

Sources & evidence

ORD record
ord-d59303dc29e2476ea578ff554c76d8b5
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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