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

HRID 242028Notes

Reaction equation

HRID 242028 reaction equation
[Li+].[OH-].[CH3:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:11][CH:12]=2)[NH:7][C:6](=[O:18])[C:5]=1[C:19]([O:21]CC)=[O:20]>CO.C1COCC1>[CH3:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([F:16])([F:17])[F:15])=[CH:11][CH:12]=2)[NH:7][C:6](=[O:18])[C:5]=1[C:19]([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66583605HCID 66583605, 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

A 2M aq. LiOH sol. (125 ml) was added to a solution of 15.0 g (50.1 mmol) ethyl 4-methyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylate in a MeOH/THF mixture (175 ml each) and the RS was subsequently heated at 60° C. for 16 h. The mixture was then concentrated in vacuo. The residue was taken up with water and adjusted to pH 2 with a 2M hydrochloric acid, followed by extraction with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. As residue 12.0 g (44.2 mmol, 88%) 4-methyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylic acid was obtained, which was used in the next step without further purification.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. extractionfollowed by extraction with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49ee063805d54042b996741be91c7df9
Source dataset
uspto-grants-2014_02
Patent number
US08653102B2

Reaction notes

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