Reaction #710570

Reaction equation

Methyl iodide

2-methylquinaldine

K2CO3

→

8-methoxy-2-methylquinoline

Solvents

acetone

Conditions

Workup

1. 1
   FiltrationThe reaction mixture was filtered
2. 2
   Otherfiltrate removed under a reduced pressure
3. 3
   OtherThe residue was purified by flash column chromatography with Hex/EA (3:1)
4. 4
   Otherrecrystallized with Hexane/EA

Procedure

Methyl iodide (10.8 g, 76.3 mmol) was added to a stirred solution of 2-methylquinaldine (1.0 g, 6.3 mmol) and K2CO3 (5.0 g, 36.2 mmol) in 30 ml acetone at RT for 10 h. The reaction mixture was filtered and filtrate removed under a reduced pressure. The residue was purified by flash column chromatography with Hex/EA (3:1) and recrystallized with Hexane/EA to give 8-methoxy-2-methylquinoline as intermediates. LHMDS (2.2 to 2.5 equiv.) was treated with a stirred solution of intermediate (1 equiv.) in THF at 0° C. for 1 h. Corresponding Br(CH2)n−1OH (1.0 to 1.2 equiv.) was added to a reaction mixture and recover to RT for further 12 to 30 h. The solvent was removed under a reduced pressure. The brown oily residue was purified by flash column chromatography with Hex/EA or DCM/EA and recrystallized by Hex/EA to afford series of compounds C.

Source