Diethyl[2-(4-nitrophenoxy)ethyl]amine → 4-(2-(Diethylamino)ethoxy)aniline

HRID 735035Notes

Reaction equation

HRID 735035 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:2].[H][H]>[Ni].CO>[CH2:16]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[CH3:17]

Participants

5

Reactant 2

HCID 88294Diethyl[2-(4-nitrophenoxy)ethyl]amineHCID 178418361HCID 178418361, compound

Product 1

HCID 4189324-(2-(Diethylamino)ethoxy)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A reaction mixture of 110.52 g (0.464 mol) of diethyl-[2-(4-nitrophenoxy)ethyl]amine and 17 g of Raney nickel in 700 mL of methanol is hydrogenated for 30 hours at 20° C. and 3 bar hydrogen. The catalyst is filtered off and the filtrate is evaporated down. Yield: 93 g (96.2% of theory); C12H20N2O (M=208.30); calc.: molecular ion peak (M)+: 209; found: molecular ion peak (M)+: 209.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated down

Sources & evidence

ORD record
ord-4c393db74af84b609910a4fff94488b2
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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