Lithium Hydroxide → 1,4-Dimethyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid

HRID 1517062Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:6](=[O:23])[N:7]([CH3:22])[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:9][C:10]=1[CH3:11])=[O:4].[OH-].[Li+]>C1COCC1.CO>[CH3:22][N:7]1[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)=[CH:9][C:10]([CH3:11])=[C:5]([C:3]([OH:4])=[O:2])[C:6]1=[O:23]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 0.60 g (1.8 mmol) of 1,4-dimethyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid methyl ester 4.0 ml of THF/MeOH (1:1) was added 11.0 ml (11.0 mmol) of lithium hydroxide solution (1 molar in water) and the reaction mixture was then heated up to 60° C. After 7 hours, the solvents were evaporated and the residue poured into crashed ice, acidified with 2N HCl and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 95:5) to give 0.53 g (94%) of the title compound as light yellow solid. MS: 310.1 (M−H−).

Workup

customthe solvents were evaporated
additionthe residue poured
extractionextracted twice with CH2Cl2
washthe organic phases were washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 95:5)

Sources & evidence

ORD record: ord-4fd2eb39fd0f4569b6de3d306315a9e2
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227613B2

Reaction notes

Loading…