Potassium Hydroxide → 2-(1-Methylethyl)-3-quinolinol

HRID 502626Notes

Reaction equation

HRID 502626 reaction equation
[CH:1]([C:4]1[C:13]([O:14]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)([CH3:3])[CH3:2].[OH-].[K+].O1CCOCC1>O>[CH:1]([C:4]1[C:13]([OH:14])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 86611057Toluene-4-sulfonic acid 2-isopropyl-quinolin-3-yl ester

Product 1

HCID 684606892-(1-Methylethyl)-3-quinolinolYield 99.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of toluene-4-sulfonic acid 2-isopropyl-quinolin-3-yl ester (1.31 g, 3.8 mmol), 0.64 g (11.4 mmol) of KOH in 10 mL of water, and 50 mL of p-dioxane was heated to refluxe for 1.5 hours until completion. The p-dioxane was removed under reduced pressure and the residue was diluted with water and acidified with 1N HCl to pH=6. The aqueous solution was extracted with ethyl acetate and the combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure to afford quantitatively 0.71 g of 2-isopropyl-quinolin-3-ol

Workup

  1. temperaturewas heated
  2. customThe p-dioxane was removed under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionThe aqueous solution was extracted with ethyl acetate
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9b92362140dd45df8c9f8b860560080f
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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