Water → Dimethyl{2-[(2-methyl-3-nitrophenyl)oxy]ethyl}amine

HRID 419322

Reaktionsgleichung

Reaktionsgleichung von HRID 419322
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].Cl.Cl[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17].C([O-])([O-])=O.[K+].[K+].O>C(O)CCC>[CH3:17][N:16]([CH3:18])[CH2:15][CH2:14][O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[CH3:1]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 795792-Methyl-3-nitrophenolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Produkt 1

HCID 59452562Dimethyl{2-[(2-methyl-3-nitrophenyl)oxy]ethyl}amineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a slurry containing 5.0 g (33 mmol) of 2-methyl-3-nitrophenol, 9.4 g (65.2 mmol) of (2-chloroethyl)dimethylamine hydrochloride, 9.0 g (65.3 mmol) of K2CO3, and 100 mL of H2O was added 100 mL of butanol and the reaction mixture was heated at 80° C. for 13 h. The reaction mixture was extracted with EtOAc and the combined organic layers were dried over MgSO4 and filtered. The solvents were removed under reduced pressure and the residue was subjected to silica gel chromatography to give 7.4 g (100%) of dimethyl{2-[(2-methyl-3-nitrophenyl)oxy]ethyl}amine as a brown oil. 1HNMR (400 MHz, DMSO-d6) δ 7.29-7.42 (m, 3H), 4.11 (t, J=5.6 Hz, 2H), 2.66 (t, J=5.6 Hz, 2H), 2.22 (s, 3H), 2.20 (s, 6H). MS (ESI+) m/z 225 [M+H].

Aufarbeitung

  1. extractionThe reaction mixture was extracted with EtOAc
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customThe solvents were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-82c8f6fcd51a4c0494a5b00260ed2a8f
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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