Sodium Hydroxide → 4-methyl-2-oxo-1-(tetrahydro-2H-pyran-4-yl)-7-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylic acid

Temperature

80 °C

To a solution of 330 mg (0.86 mmol) ethyl 4-methyl-2-oxo-1-(tetrahydro-2H-pyran-4-yl)-7-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylate in ethanol (6 ml) and water (0.6 ml) was added 140 mg (3.45 mmol) NaOH at RT. The reaction mixture was stirred at 80° C. for 16 h. Then the mixture was evaporated to dryness and the residue was diluted with water (5 ml) and acidified with 2N HCl to pH ˜3. The aq. part was extracted with ethyl acetate (3×10 ml). The combined organic layers were washed with water (10 ml), brine (10 ml), dried over anhydrous Na2SO4 and concentrated in vacuum to give 280 mg (0.79 mmol, 91%) 4-methyl-2-oxo-1-(tetrahydro-2H-pyran-4-yl)-7-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylic acid which is used in the next step without further purification.

1. customThen the mixture was evaporated to dryness
2. additionthe residue was diluted with water (5 ml)
3. extractionThe aq. part was extracted with ethyl acetate (3×10 ml)
4. washThe combined organic layers were washed with water (10 ml), brine (10 ml)
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated in vacuum

ORD record

ord-ab879f381e2c4ec8a12873380c1096c9

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653102B2