Reaktion #303946

ord-8f2e8a762f1149c0943d96dec0343968

Reaktionsgleichung

COc1ccc(CNCc2cc3cccc(C)c3nc2-c2ccccc2C(F)(F)F)cc1
N-(4-methoxybenzyl)(8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanamine
O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].[Ce+4].[NH4+]
ammonium cerium(iv) nitrate
→
Cc1cccc2cc(CN)c(-c3ccccc3C(F)(F)F)nc12
(8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanamine

Edukte

COc1ccc(CNCc2cc3cccc(C)c3nc2-c2ccccc2C(F)(F)F)cc1
N-(4-methoxybenzyl)(8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanamine
O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].[Ce+4].[NH4+]
ammonium cerium(iv) nitrate

Reagenzien

Keine

Lösungsmittel

CC#N.O
CH3CN—H2O

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePrepared
  2. 2
    SonstigeAfter purification

Vorschrift

Prepared according to Procedure G using N-(4-methoxybenzyl)(8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanamine (1.1427 g, 2.62 mmol, 1 eq) and ammonium cerium(iv) nitrate (3.59 g, 6.55 mmol, 2.5 eq) in CH3CN—H2O (2:1, 12 mL). After purification, (8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanamine was obtained as brown syrup. 1H NMR (DMSO-d6) δ ppm 8.47 (1H, s), 7.91 (1H, d, J=7.4 Hz), 7.84 (1H, d, J=7.4 Hz), 7.67-7.81 (2H, m), 7.47-7.62 (3H, m), 3.46-3.70 (2H, m), 2.61 (3H, s), 1.86 (2H, br. s.). Mass Spectrum (ESI) m/e=317.0 (M+1).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08193199B2uspto-grants-2012_06