Reaction #84110

Reaction equation

6-methoxyquinolin-2-ol

POCl3

→

2-chloro-6-methoxyquinoline

Yield 86.0%

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved in EtOAc (50 mL)
3. 3
   Washthe organic layer was washed with saturated NaHCO3 (30 mL×2)
4. 4
   Dryingdried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   Otherto give the crude product, which
8. 8
   Otherwas purified by silica gel column (PE/EtOAc=10/1)

Procedure

A solution of 6-methoxyquinolin-2-ol (400 mg, 2.29 mmol) in POCl3 (5.0 mL) was refluxed for 2 hours. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc (50 mL), the organic layer was washed with saturated NaHCO3 (30 mL×2), dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by silica gel column (PE/EtOAc=10/1) to give 2-chloro-6-methoxyquinoline (380 mg, yield 86%) as a solid. 1H NMR (CDCl3 400 MHz): δ 7.92 (d, J=8.4 Hz, 1H), 7.85 (d, J=9.2 Hz, 1H), 7.32-7.25 (m, 2H), 7.00 (d, J=2.4 Hz, 1H), 3.86 (s, 3H).

Source