Lithium Hydroxide → 2-Methoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid
Reaction equation
[Li+].[OH-].C([O:5][C:6]([C:8]1[C:9](Cl)=[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.C1C[O:29][CH2:28]C1>>[CH3:28][O:29][C:9]1[C:8]([C:6]([OH:5])=[O:7])=[C:17]([CH3:18])[C:16]2[C:11](=[CH:12][C:13]([C:19]([F:22])([F:21])[F:20])=[CH:14][CH:15]=2)[N:10]=1Participants
Conditions
- Temperature
- 70 °C
Procedure
A 2M aq. LiOH sol. (12 ml) was added to a solution of 1.3 g (4.0 mmol) 2-chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester (synthesis see Example 3 Section a)) in a MeOH/THF mixture (in each case 10 ml) and the solution was subsequently heated to 70° 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, adjusted to 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. 754 mg (2.6 mmol, 66%) 2-methoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid was obtained as a residue. The raw product was further converted without additional purification.
Workup
- customsynthesis
- 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-f73e9502fe34427f9fefd0e6cff4aeba
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653101B2
Reaction notes
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