Ammonium cerium (IV) nitrate → (2-(2-Fluoro-6-methoxyphenyl)-8-methylquinolin-3-yl)methanamine

HRID 216768

Reaction equation

HRID 216768 reaction equation
COC1C=CC(C[NH:8][CH2:9][C:10]2[C:11]([C:21]3[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=3[F:29])=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:20])=CC=1.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>CC#N.O>[F:29][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:21]=1[C:11]1[C:10]([CH2:9][NH2:8])=[CH:19][C:18]2[C:13](=[C:14]([CH3:20])[CH:15]=[CH:16][CH:17]=2)[N:12]=1

Participants

4

Reactant 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 57707905N-(4-methoxybenzyl)(2-(2-fluoro-6-methoxyphenyl)-8-methylquinolin-3-yl)methanamine

Product 1

HCID 57707963(2-(2-Fluoro-6-methoxyphenyl)-8-methylquinolin-3-yl)methanamine

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Prepared according to Procedure G using N-(4-methoxybenzyl)(2-(2-fluoro-6-methoxyphenyl)-8-methylquinolin-3-yl)methanamine (1.1795 g, 2.8320 mmol, 1 eq) and ammonium cerium(iv) nitrate (5.434 g, 9.912 mmol, 3.5 eq) in CH3CN—H2O (2:1, 13 mL). After purification, (2-(2-fluoro-6-methoxyphenyl)-8-methylquinolin-3-yl)methanamine was obtained as yellow sticky solid. 1H NMR (DMSO-d6) δ ppm 8.41 (1H, s), 7.82 (1H, d, J=7.4 Hz), 7.55-7.60 (1H, m), 7.45-7.54 (2H, m), 7.03 (1H, d, J=8.2 Hz), 6.92-7.00 (1H, m), 3.71 (3H, s), 3.59 (2H, q, J=16.6 Hz), 2.64 (3H, s), 1.88 (2H, br. s.). Mass Spectrum (ESI) m/e=297.1 (M+1).

Workup

  1. customPrepared
  2. customAfter purification

Sources & evidence

ORD record
ord-fbb5ea72c1f74f98a4676afebaa36f38
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Linked notes

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