Sodium Bicarbonate → Toluene-4-sulfonic acid 2-isopropyl-quinolin-3-yl ester
Reaction equation
O[C:2]([C:5]1[C:14]([O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)([CH3:4])[CH3:3].C([O-])(O)=O.[Na+]>C(O)=O.[Zn]>[CH:2]([C:5]1[C:14]([O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:17])=[O:18])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)([CH3:4])[CH3:3]Participants
Procedure
Toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester (3.75 g, 10.5 mmol) was stirred in 50 mL of formic acid for 10 minutes, and zinc dust (3.43 g, 5.25 mmol) was added. The reaction mixture was stirred for four hours and then was added cautiously to a mixture of 100 mL aqueous saturated NaHCO3 and 100 g of ice. The resulting aqueous mixture was neutralized to pH7 by addition of aqueous saturated NaHCO3, and was extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography using silica eluting with 10% ethyl acetate in hexanes to afford 1.35 g of toluene-4-sulfonic acid 2-isopropyl-quinolin-3-yl ester.
Workup
- extractionwas extracted with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-c07a2b81b6724bf7a03e9e9481bef52e
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776872B2
Reaction notes
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