Acetic Acid → 3-{6-[1-Methyl-1-(methylsulfonyl)ethyl]quinolin-8-yl}benzoic acid

HRID 1455660Notes

Reaction equation

HRID 1455660 reaction equation
[CH3:1][C:2]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=3)[C:21]([O:23]C)=[O:22])[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([S:4]([CH3:7])(=[O:6])=[O:5])[CH3:3].[Li+].[OH-].CC(O)=O>C1COCC1.O>[CH3:3][C:2]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=3)[C:21]([OH:23])=[O:22])[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([S:4]([CH3:7])(=[O:5])=[O:6])[CH3:1]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 68887704Methyl 3-{6-[1-methyl-1-(methylsulfonyl)ethyl]quinolin-8-yl}benzoate

Product 1

HCID 218655663-{6-[1-Methyl-1-(methylsulfonyl)ethyl]quinolin-8-yl}benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ester from step 1 in THF (0.08M) was added LiOH (2N, 5 eq). The reaction mixture was stirred at rt for 5 h, acidified with AcOH, diluted with water and extracted with CH2Cl2. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The title compound was isolated by filtration from Hexane/ether as a solid.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d98403e5b5d14f63961873d6ab02327e
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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