N-Methyl-4-anisidine → (4-Methoxy-phenyl)-methyl-(2-trifluoromethyl-quinolin-4-yl)-amine

HRID 1876171

Reaction equation

HRID 1876171 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([NH:22][CH3:23])=[CH:20][CH:19]=1>C(O)(=O)C>[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([N:22]([CH3:23])[C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 22250N-Methyl-4-anisidineHCID 27367094-Chloro-2-(trifluoromethyl)quinoline

Product 1

HCID 68516813(4-Methoxy-phenyl)-methyl-(2-trifluoromethyl-quinolin-4-yl)-amineYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 4-chloro-2-(trifluoromethyl)quinoline 0.232 g (1.0 mmol) and 4-methoxy-N-methylaniline 0.137 g (1.0 mmol) in glacial acetic acid 3 mL was stirred at 100-110° C. for 24 h. The reaction mixture was directly subjected to gradient column chromatography (EtOAc/hexanes, 0% to 50%) to give the titled compound in 70% yield. 1H NMR (CDCl3, 400 MHz): δ 8.11-8.08 (m, 1H), 7.62-7.58 (m, 1H), 7.58-7.55 (m, 1H), 7.27-7.22 (m, 2H), 6.97 (d, 2H, J=9.0 Hz), 6.84 (d, 2H, J=9.0 Hz), 3.79 (s, 3H), 3.49 (s, 3H). m/z: 333.2 (M+1).

Sources & evidence

ORD record
ord-912bc5ab8f1945ac86e34b93be8aac07
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Linked notes

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