Lithium Hydroxide → HCID 58154631, compound

HRID 2359405Notes

Reaction equation

HRID 2359405 reaction equation
[F:1][C:2]([F:25])([F:24])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([C:20]([O:22]C)=[O:21])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1.[OH-].[Li+]>C1COCC1.O>[F:25][C:2]([F:1])([F:24])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58154739HCID 58154739, compound

Product 1

HCID 58154631HCID 58154631, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of Methyl 2-(3-(trifluoromethoxy)phenyl)quinoline-8-carboxylate (1.1 g, 3.16 mmol) dissolved in THF (20 mL) was added a mixture of lithium hydroxide (227 mg, 9.5 mmol) in water (15 mL). The reaction was stirred 70 hours. The reaction mixture was concentrated to remove the THF and the aqueous solution was adjusted to pH=1 with 4N HCl (aq). The solid was collected by filtration, rinsed with water, and dried under vacuum to obtain 2-(3-(trifluoromethoxy)phenyl)quinoline-8-carboxylic acid as a tan solid (973 mg, 92% yield).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. customto remove the THF
  4. filtrationThe solid was collected by filtration
  5. washrinsed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-4768c4a6a23f4e6ca1b9bc2f7f7622b9
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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