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

HRID 2093716Notes

Reaction equation

[Li+].[OH-].C[O:4][C:5]([C:7]1[C:8]([CH2:22][O:23][CH3:24])=[N:9][C:10]2[C:15]([C:16]=1[CH3:17])=[CH:14][CH:13]=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=2)=[O:6]>C1COCC1>[CH3:24][O:23][CH2:22][C:8]1[C:7]([C:5]([OH:6])=[O:4])=[C:16]([CH3:17])[C:15]2[C:10](=[CH:11][C:12]([C:18]([F:21])([F:20])[F:19])=[CH:13][CH:14]=2)[N:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A 2M aq. LiOH sol. (9.3 ml) was added to a solution of 980 mg (3.1 mmol) 2-(methoxymethyl)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid methyl ester in THF (25 ml) and the mixture was subsequently heated to 60° C. for 16 h. The THF was removed as far as possible in a vacuum and the obtained aqueous solution was washed with ether, the pH was set to 2 with 2M hydrochloric acid and dilution was performed with EtOAc. The organic phase was separated and washed with brine, dried over MgSO4 and concentrated in a vacuum. 612 mg (2.0 mmol, 66%) 2-(methoxymethyl)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid was obtained as a residue. The raw product was further converted without additional purification.

Workup

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

Sources & evidence

ORD record: ord-e9aa2656e1464dd9ac8f7baa4755bfef
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445512B2

Reaction notes

Loading…