Dichloromethane methanol → 3-Chloro-4-(2-diethylaminoethoxy)phenylamine

HRID 735077Notes

Reaction equation

HRID 735077 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:10][CH3:11])[CH2:8][CH3:9].ClCCl.CO>CO>[Cl:1][C:2]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:8][CH3:9])[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 21226129Dichloromethane methanolHCID 68816504[2-(2-Chloro-4-nitro-phenoxy)-ethyl]-diethyl-amine

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared analogously to Example 3.1.b. from [2-(2-chloro-4-nitrophenoxy)ethyl]diethylamine in methanol in a reaction time of 4.5 hours. Yield: 36.12 g (81.8% of theory); C12H19ClN2O (M=242.75); calc.: molecular ion peak (M+H)+: 243/245; found: molecular ion peak (M+H)+: 243/245; Rf value: 0.36 (silica gel, dichloromethane/methanol (90:10)).

Workup

  1. customPrepared analogously to Example 3.1.b
  2. customin a reaction time of 4.5 hours

Sources & evidence

ORD record
ord-1e32c9ca2e2747508faa6d084ba64cd6
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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