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

HRID 242116Notes

Reaction equation

HRID 242116 reaction equation
[Li+].[OH-].C([O:5][C:6]([C:8]1[C:9]([OH:23])=[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>[OH: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:21])([F:20])[F:22])=[CH:14][CH:15]=2)[N:10]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178470056HCID 178470056, compound

Product 1

HCID 665836552-Hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acidYield 88.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

2M aq. LiOH sol. (125 ml) was added to a solution of 15.0 g (50.1 mmol) 2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in a MeOH/THF mixture (in each case 175 ml) and the solution was subsequently heated to 60° C. for 16 h. The solution was subsequently concentrated in a vacuum. The residue was taken up with water and adjusted to pH 2 with a 2M hydrochloric acid. Extraction was then performed with EtOAc. The organic phase was washed with brine, dried over MgSO4 and concentrated in a vacuum. 12.0 g (44.2 mmol, 88%) 2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid was obtained as a residue. The raw product was further converted without additional purification.

Workup

  1. concentrationThe solution was subsequently concentrated in a vacuum
  2. extractionExtraction
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-5ca0920d1c5444d2a55a32c4b1886128
Source dataset
uspto-grants-2014_02
Patent number
US08653101B2

Reaction notes

Loading…