3-Fluorobenzylamine → HCID 86645341, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].[Cl:10][C:11]1[C:20]([C:21](Cl)=[O:22])=[C:19]([CH3:24])[C:18]2[C:13](=[CH:14][C:15]([C:25]([F:28])([F:27])[F:26])=[CH:16][CH:17]=2)[N:12]=1>O1CCOCC1>[Cl:10][C:11]1[C:20]([C:21]([NH:6][CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=2)=[O:22])=[C:19]([CH3:24])[C:18]2[C:13](=[CH:14][C:15]([C:25]([F:26])([F:28])[F:27])=[CH:16][CH:17]=2)[N:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2.9 g (23.4 mmol) 3-fluorobenzylamine was added dropwise at RT to a solution of 6.0 g (19.5 mmol) 2-chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carbonyl chloride in dioxane (35 ml). The mixture was then stirred for 60 min at RT and then quenched with water. The reaction solution was extracted with EE and the organic phase was washed with a 1M aqueous NH4Cl solution and brine, dried over MgSO4, filtered and concentrated to small volume under vacuum. Crystallisation of the residue (EE) yielded 6.4 g (16.1 mmol, 83%) 2-chloro-N-[(3-fluorophenyl)-methyl]-4-methyl-7-(trifluoromethyl)-quinoline-3-carboxamide.