N,N-Diethyl-2-(4-methoxy-3-nitrophenoxy)ethylamine → 5-(2-(Diethylamino)ethoxy)-2-methoxybenzenamine

HRID 1042707Notes

Reaction equation

HRID 1042707 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([N+:17]([O-])=O)[CH:10]=1)[CH2:4][CH3:5])[CH3:2]>C(O)C.[Pd]>[CH2:4]([N:3]([CH2:1][CH3:2])[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([NH2:17])[CH:10]=1)[CH3:5]

Participants

4

Reactant 1

HCID 59427849N,N-Diethyl-2-(4-methoxy-3-nitrophenoxy)ethylamine

Product 1

HCID 594278525-(2-(Diethylamino)ethoxy)-2-methoxybenzenamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N,N-diethyl-2-(4-methoxy-3-nitrophenoxy)ethylamine (0.29 g, 1.1 mmol) was hydrogenated over Pd (5% on C, 50% wet, 0.12 g) in ethanol (5 ml) for 16 hours. The catalyst was filtered off and the solvent removed under reduced pressure to afford the title compound as a red oil. MS (m/z)=239 (M+H+); Calc'd for C13H22N2O2=238.33.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d44a5943536547f0a4704a61b0e4be41
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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