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

HRID 242039Notes

Reaction equation

[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]([CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:4](=[O:22])[C:3]=1[C:23]([O:25]CC)=[O:24].[OH-].[Na+]>C(O)C.O>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:14])([F:13])[F:15])=[CH:9][CH:10]=2)[N:5]([CH:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[C:4](=[O:22])[C:3]=1[C:23]([OH:25])=[O:24]

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-ab879f381e2c4ec8a12873380c1096c9
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653102B2

Reaction notes

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