Lithium Hydroxide → HCID 66583917, compound

HRID 2093718Notes

Reaction equation

HRID 2093718 reaction equation
[Li+].[OH-].C([O:5][C:6]([C:8]1[C:9]([CH2:23][C:24]([CH3:27])([CH3:26])[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>CO.O1CCOCC1>[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]([CH2:23][C:24]([CH3:27])([CH3:25])[CH3:26])[C:8]=1[C:6]([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66583981HCID 66583981, compound

Product 1

HCID 66583917HCID 66583917, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A 2M aq. LiOH sol. (10 ml) was added to a solution of 1.1 g (3.0 mmol) 4-methyl-2-neopentyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in a MeOH/1,4-dioxane mixture (in each case 10 ml) and the mixture was subsequently heated to 80° C. for 72 h. The organic solvents were removed as far as possible in a vacuum and the obtained aqueous solution was washed with ether, 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. 0.8 g (2.5 mmol, 82%) 4-methyl-2-neopentyl-7-(trifluoromethyl)quinoline-3-carboxylic acid was obtained as a residue. The raw product was further converted without additional purification.

Workup

  1. customThe organic solvents were removed as far as possible in a vacuum
  2. washthe obtained aqueous solution was washed with ether
  3. additiondiluted with EtOAc
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-df18a34872e04c0a93a5a970747fb6a9
Source dataset
uspto-grants-2013_05
Patent number
US08445512B2

Reaction notes

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