N-Methylaniline → 2-(N-Methylanilino)ethanol

HRID 1053555

Reaktionsgleichung

Reaktionsgleichung von HRID 1053555
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH2:10][CH2:11][OH:12].C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:10][CH2:11][OH:12]

Komponenten

5

Edukt 3

HCID 7515N-MethylanilineHCID 12225IodoethanolHCID 81531Diisopropylethylamine

Produkt 1

HCID 623402-(N-Methylanilino)ethanolAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

N-methylaniline (5 mls, 0.05 mol) was reacted with 2-Iodoethanol (3.599 mls, 0.05 mol) and diisopropylethylamine (8.039 mls, 0.05 mol) in ACN at 70° C. for 16 hours. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/EtOAc to provide the compound as a yellow orange oil, 2a (4.48 g, 0.03 mol, 64.5% yield). 1H NMR (400 MHz, Chloroform-d) δ 7.27-7.15 (m, 2H), 6.81-6.67 (m, 3H), 3.74 (t, J=5.8 Hz, 2H), 3.42 (t, J=5.8 Hz, 2H), 2.92 (s, 3H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography with hexane/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-8e1eea2535334931a39c0c65d9e381a5
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394233B2

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