Sodium ethoxide → 2-Ethoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester

HRID 242114Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

1.2 g (17.8 mmol) sodium ethylate was added to a solution of 5.1 g (16.1 mmol) 2-chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in EtOH (20 ml) at RT. The RS was subsequently heated to 60° C. for 4 h and then stirred for 16 h at RT. The solution was then diluted with water and EtOAc. The organic phase was separated and washed with a 4N aq. NH4Cl sol., dried over MgSO4 and concentrated in a vacuum. 5.1 g (15.6 mmol, 97%) 2-ethoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester was obtained as a residue. The raw product was further converted without additional purification.

Workup

customThe organic phase was separated
washwashed with a 4N aq. NH4Cl sol.
dry with materialdried over MgSO4
concentrationconcentrated in a vacuum

Sources & evidence

ORD record: ord-d654cc9f06ba42b683b4abe47dbe974f
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653101B2

Reaction notes

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