Reaktion #601120

Reaktionsgleichung

7-((4-fluorobenzyl)oxy)quinoline-3-carbonyl chloride

N,O-dimethylhydroxylamine hydrochloride

DIPEA

7-((4-Fluorobenzyl)oxy)-N-methoxy-N-methylquinoline-3-carboxamide

→

title compound

Ausbeute 67.0%

1-(7-((4-Fluorobenzyl)oxy)quinolin-3-yl)ethanone

Ausbeute 67.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenbefore being concentrated onto silica
2. 2
   SonstigePurification (FCC, SiO2, 0-80%, EtOAc/hexanes)

Vorschrift

7-((4-Fluorobenzyl)oxy)-N-methoxy-N-methylquinoline-3-carboxamide. To a solution of 7-((4-fluorobenzyl)oxy)quinoline-3-carbonyl chloride in DCM (14 mL) was added N,O-dimethylhydroxylamine hydrochloride (207 mg, 2.12 mmol) and DIPEA (0.739 mL, 4.23 mmol). The reaction was stirred for 15 minutes at ambient temperature before being concentrated onto silica. Purification (FCC, SiO2, 0-80%, EtOAc/hexanes) afforded the title compound as a white solid (324 mg, 67%). 1H NMR (400 MHz, CDCl3) δ 9.18 (d, J=2.0 Hz, 1H), 8.54 (d, J=1.6 Hz, 1H), 7.81 (d, J=9.0 Hz, 1H), 7.52 (d, J=2.0 Hz, 1H), 7.51-7.44 (m, 2H), 7.32 (dd, J=2.3, 9.0 Hz, 1H), 7.11 (t, J=8.8 Hz, 2H), 5.21 (s, 2H), 3.59 (s, 3H), 3.45 (d, J=0.8 Hz, 3H). [M+H]=341.3.

Quelle