Hydrochloric Acid → (S)-7-(2-methoxypropoxy)-2-methylquinoline

To a stirred solution of 2-methylquinolin-7-ol (1.00 g, 6.28 mmol), PPh3 (4.12 g, 15.7 mmol) and (S)-2-methoxypropan-1-ol (0.679 g, 7.54 mmol) in THF (60 mL) was added dropwise diisopropyl azodicarboxylate (2.05 mL, 10.1 mmol) at 0° C. under nitrogen. The reaction mixture was stirred at ambient temperature overnight. The reaction was then heated at 50° C. for additional 2 hours. After cooling, to the reaction were added 4N HCl (3.1 mL), water (100 mL) and EtOAc (200 mL). The aqueous layer was separated and washed with EtOAc (100 mL). The aqueous was neutralized with ammonium hydroxide to about pH 9, extracted with EtOAc, washed with brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1:1 hexane/EtOAc) to give (S)-7-(2-methoxypropoxy)-2-methylquinoline (0.738 g, 51%).

1. temperatureThe reaction was then heated at 50° C. for additional 2 hours
2. temperatureAfter cooling, to the reaction
3. customThe aqueous layer was separated
4. washwashed with EtOAc (100 mL)
5. extractionextracted with EtOAc
6. washwashed with brine
7. customdried
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by flash chromatography on silica gel (1:1 hexane/EtOAc)

ORD record

ord-ed0c4bf009384be792b830996bf2be43

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889704B2