4-Nitrophenol → Diethyl[2-(4-nitrophenoxy)ethyl]amine

HRID 2067862Notes

Reaction equation

HRID 2067862 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23]>C1(C)C=CC=CC=1>[CH2:20]([N:21]([CH2:24][CH3:25])[CH2:22][CH2:23][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:19]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10796Cesium carbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochloride

Product 1

HCID 88294Diethyl[2-(4-nitrophenoxy)ethyl]amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-nitro-phenol 1 (36.0 mmol) in toluene (40 mL) is added cesium carbonate (53.8 mmol) and (2-chloro-ethyl)-diethyl-amine hydrochloride (28.7 mmol). The reaction mixture is heated at 100° C. for 2 h then cooled to rt. The solid is filtered under vacuum and washed with warm toluene. The filtrate is concentrated to afford diethyl-[2-(4-nitro-phenoxy)-ethyl]-amine 2 and used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 8.10-8.08 (m, 2H), 6.86-6.84 (m, 2H), 4.05 (t, J=4.0 Hz, 2H), 2.81 (t, J=4.0 Hz), 2.55 (q, J=8.0 Hz, 4H), 0.98 (t, J=8.0 Hz, 6H). MS (m/z) (M+1)+: 239.3.

Workup

  1. temperaturethen cooled to rt
  2. filtrationThe solid is filtered under vacuum
  3. washwashed with warm toluene
  4. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-387cc260d92d4d4aada86ec2c5f1dda4
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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