Pyridine → 2-(2-Oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)ethyl 4-methylbenzenesulfonate

HRID 1023202Notes

Reaction equation

HRID 1023202 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2.N1C=CC=CC=1.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>C(Cl)Cl.CCOC(C)=O>[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:1][CH2:2][CH2:3][O:4][C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]3)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 133921376-(2-Hydroxyethoxy)-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 866804362-(2-Oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)ethyl 4-methylbenzenesulfonateYield 27%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(2-hydroxyethoxy)-3,4-dihydroquinolin-2(1H)-one (0.15 g, 0.724 mmol) in DCM (2 mL) was added pyridine (0.117 mL, 1.448 mmol) and 4-methylbenzene-1-sulfonyl chloride (0.152 g, 0.796 mmol) and the reaction was stirred for 4 h. The reaction was diluted with EtOAc (25 mL), washed with 0.1 N HCl (10 mL), brine (10 mL), and sat. NaHCO3 solution (10 mL). The organic layer was dried over sodium sulfate, evaporated to dryness, and purified by flash chromatography on silica gel (4 g, 50% EtOAC in hexanes) to yield 2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)ethyl 4-methylbenzenesulfonate (0.07 g, 27%).

Workup

  1. washwashed with 0.1 N HCl (10 mL), brine (10 mL), and sat. NaHCO3 solution (10 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness
  4. custompurified by flash chromatography on silica gel (4 g, 50% EtOAC in hexanes)

Sources & evidence

ORD record
ord-c2c2260cec474d4aae94e5d301266eb1
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

Loading…