Reaktion #506504

Reaktionsgleichung

2-methyl-3-nitrophenol

(2-chloroethyl)dimethylamine hydrochloride

K2CO3

H2O

→

dimethyl{2-[(2-methyl-3-nitrophenyl)oxy]ethyl}amine

Ausbeute 100.0%

Lösungsmittel

butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe reaction mixture was extracted with EtOAc
2. 2
   Trocknenthe combined organic layers were dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   SonstigeThe solvents were removed under reduced pressure

Vorschrift

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].

Quelle