Hydrochloric Acid → Toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester
Reaction equation
[C:1]([C:4]1[C:13]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)(=[O:3])[CH3:2].[CH3:25][Mg]Cl.[NH4+].[Cl-].Cl>C1COCC1>[OH:3][C:1]([C:4]1[C:13]([O:14][S:15]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)(=[O:17])=[O:16])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)([CH3:25])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Toluene-4-sulfonic acid 2-acetyl-quinolin-3-yl ester (3.58 g, 10.5 mmol) in 40 mL of THF was cooled to around −20 to −25° C. Methyl magnesium chloride (5.25 mL of 3M solution in THF) was added dropwise over a period of 10 minutes. The reaction mixture was allowed to stir 18 hours at ambient temperature, and then was poured into saturated aqueous NH4Cl and acidified with 1N HCl to pH 5. The resulting mixture was extracted with ethyl acetate and the combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated to dryness under reduced pressure to give 3.75 g of toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester as an oil that solidified on standing.
Workup
- extractionThe resulting mixture was extracted with ethyl acetate
- washthe combined organic phases were washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-7b93517d03ef4298bef0557c4050d7aa
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776872B2
Reaction notes
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