Sulfuric Acid → 3-[4-(6-bromo-4,4-dimethyl-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethoxy)phenyl]hex-4-ynoic acid

HRID 40487Notes

Reaction equation

HRID 40487 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:26]#[C:27][CH3:28])[CH2:21][C:22]([O:24]C)=[O:23])=[CH:16][CH:15]=1)[C:7](=[O:29])[CH2:6][C:5]2([CH3:31])[CH3:30].[Li+].[OH-].OS(O)(=O)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:26]#[C:27][CH3:28])[CH2:21][C:22]([OH:24])=[O:23])=[CH:16][CH:15]=1)[C:7](=[O:29])[CH2:6][C:5]2([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3939Lithium HydroxideHCID 58031732HCID 58031732, compound

Product 1

HCID 547669273-[4-(6-bromo-4,4-dimethyl-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethoxy)phenyl]hex-4-ynoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

91 mg of methyl 3-[4-(6-bromo-4,4-dimethyl-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethoxy)-phenyl]hex-4-ynoate were dissolved in 1.4 ml of tetrahydrofuran, and 1N LiOH solution was added. The experiment was stirred at room temperature for 2 hours and left to stand at room temperature overnight. Subsequently, 2N H2SO4 was used to adjust the pH to 1 and the mixture was extracted with 80 ml of ethyl acetate. The organic phase was removed and dried over MgSO4, filtered and then concentrated under reduced pressure. The residue was purified by means of RP-HPLC. This gave 27.0 mg of 3-[4-(6-bromo-4,4-dimethyl-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethoxy)phenyl]hex-4-ynoic acid,

Workup

  1. waitleft
  2. waitto stand at room temperature overnight
  3. extractionthe mixture was extracted with 80 ml of ethyl acetate
  4. customThe organic phase was removed
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by means of RP-HPLC

Sources & evidence

ORD record
ord-601f2a4003a9480f9b14e33ee8f80a2e
Source dataset
uspto-grants-2013_09
Patent number
US08530413B2

Reaction notes

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