Trifluoroacetic acid → N-METHYLQUINOLIN-3-AMINE
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH2:11])[CH:2]=1.F[C:13](F)(F)C(O)=O>C(OCC)(OCC)OCC>[CH3:13][NH:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of quinolin-3-ylamine (5.2 g, 36.1 mmol) and trifluoroacetic acid (catalytic) in triethyl orthoformate (30 mL) was heated at reflux for 6 hours. The solvent was evaporated in vacuo, and the residue was dissolved in ethanol (50 mL). Sodium borohydride tablets (2.5 g, 0.203 mol) was added to the solution, and the resultant mixture was stirred at room temperature for 2.5 days. The mixture was partitioned between water and dichloromethane. The organic layer was separated, washed with water and dried over sodium sulfate. The solvent was evaporated in vacuo, to give the product, 5.35 g (94%), an oil, which crystallized on standing. MS: m/z 159 (MH+). 1H NMR (CDCl3): 2.90 (d, 3 H), 4.15 (br s, 1 H), 6.97 (d, 1 H), 7.36-7.47 (m, 2 H), 7.55-7.65 (m, 1 H), 7.91-7.96 (m, 1 H) and 8.42 (d, 1 H).