Lithium Hydroxide → 2-Ethoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid

HRID 242115Notes

Reaction equation

[Li+].[OH-].C([O:5][C:6]([C:8]1[C:9]([O:23][CH2:24][CH3:25])=[N:10][C:11]2[C:16]([C:17]=1[CH3:18])=[CH:15][CH:14]=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:12]=2)=[O:7])C>CO.C1COCC1>[CH2:24]([O:23][C:9]1[C:8]([C:6]([OH:7])=[O:5])=[C:17]([CH3:18])[C:16]2[C:11](=[CH:12][C:13]([C:19]([F:22])([F:20])[F:21])=[CH:14][CH:15]=2)[N:10]=1)[CH3:25]

Participants

Conditions

Temperature: 60 °C

Procedure

2M aq. LiOH sol. (38 ml) was added to a solution of 5.1 g (15.5 mmol) 2-ethoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in a MeOH/THF mixture (in each case 38 ml) and subsequently heated to 60° C. for 16 h. The organic solvents were removed as far as possible in a vacuum and the obtained aqueous solution was washed with EtOAc, set at pH 2 with 2M hydrochloric acid and diluted with EtOAc. The organic phase was separated and washed with brine, dried over MgSO4 and concentrated in a vacuum. 4.4 g (14.7 mmol, 95%) 2-ethoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid was obtained as a residue. The raw product was further converted without additional purification.

Workup

customThe organic solvents were removed as far as possible in a vacuum
washthe obtained aqueous solution was washed with EtOAc
additiondiluted with EtOAc
customThe organic phase was separated
washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated in a vacuum

Sources & evidence

ORD record: ord-7f0117f3b386454fa26c5a0e537b3351
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653101B2

Reaction notes

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