Sodium Hydroxide → (E)-4-methyl-2-(prop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid

HRID 2093722Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

560 mg (13.9 mmol) NaOH flocs were added to a solution of 450 mg (1.4 mmol) (E)-4-methyl-2-(prop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in a water/EtOH mixture (in each case 21 ml) at 0° C. The mixture was subsequently heated to 90° C. for 16 h. It was then concentrated in a vacuum and the residue was taken up with water (20 ml) and washed with EtOAc. Thereafter, the aqueous phase was set to pH ˜2 with a 2M hydrochloric acid and extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated in a vacuum. 350 mg (1.2 mmol, 85%) (E)-4-methyl-2-(prop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid was obtained as a residue. The raw product was further converted without additional purification.

Workup

concentrationIt was then concentrated in a vacuum
washwashed with EtOAc
extractionextracted with EtOAc
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated in a vacuum

Sources & evidence

ORD record: ord-7f07e6afef71460e9bd68932aef8cc35
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445512B2

Reaction notes

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