[2-(2-Chloro-4-nitro-phenoxy)-ethyl]-diethyl-amine → 3-Chloro-4-(2-diethylaminoethoxy)phenylamine

HRID 1820858Notes

Reaction equation

HRID 1820858 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:16]([O-])=O)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13]>CO.[H][H].[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13]

Participants

5

Reactant 1

HCID 68816504[2-(2-Chloro-4-nitro-phenoxy)-ethyl]-diethyl-amine

Product 1

HCID 167916763-Chloro-4-(2-diethylaminoethoxy)phenylamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 178418361HCID 178418361, compoundCatalystHCID 887MethanolSolvent

Procedure

41.0 g (150 mmol) of 3-chloro-4-(2-diethylaminoethoxy)nitrobenzene (IV.1.a) is dissolved in 250 mL of methanol and hydrogenated for 5 hours at ambient temperature at a pressure of 50 psi with hydrogen and 4.0 g of Raney nickel as catalyst. Then the catalyst is filtered off and the solvent is eliminated. The residue is recrystallized from petroleum ether and dried in vacuo. Yield: 33.0 g (91% of theory); Rf value: 0.40 (silica gel, methylene chloride/methanol/ammonia=9:1:0.01); C12H19ClN2O; EII mass spectrum: m/z=243/245 [M+H]+.

Workup

  1. filtrationThen the catalyst is filtered off
  2. customThe residue is recrystallized from petroleum ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-8f22c897a9b4485997536e20079c7846
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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