Hydrochloric Acid → 5-Hydroxymethyl-6-(2-hydroxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Under argon atmosphere, lithium aluminum hydride (1.48 g, 39.0 mmol) was suspended in anhydrous tetrahydrofuran (30 mL). A solution of 2,2,4-Trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one (Reference Compound No. 1-1, 3.80 g, 13.0 mmol) in anhydrous tetrahydrofuran (40 mL) was added dropwise at 0° C. and the reaction mixture was stirred at the same temperature for 1 hour. Ethyl acetate (15 mL) and water (5 mL) were added dropwise successively to the reaction mixture and then 0.2 N aqueous HCl solution (350 mL) was added thereto. The whole was extracted with ethyl acetate (300 mL, 100 mL). The combined organic layer was washed with water (300 mL) and saturated brine (100 mL) successively, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the titled reference compound (4.01 g) as a pale brown solid. (Yield quantitative)

1. extractionThe whole was extracted with ethyl acetate (300 mL, 100 mL)
2. washThe combined organic layer was washed with water (300 mL) and saturated brine (100 mL) successively
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent was removed under reduced pressure

ORD record

ord-48cd91b92307441fbece6f438d52d4ca

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017775B2