2-Mercaptoethanol → 2-(6-Methoxy-quinolin-3-ylsulfanyl)-ethanol

HRID 2279371Notes

Reaction equation

HRID 2279371 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].Br[C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([O:16][CH3:17])=[CH:11][CH:10]=2.[H-].[Na+].C(OCC)(=O)C>CN(C)C=O.CCCCCC>[CH3:17][O:16][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:1][CH2:2][CH2:3][OH:4])=[CH:15]2

Participants

7

Reactant 4

HCID 15672-MercaptoethanolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 147585873-Bromo-6-methoxyquinoline

Product 1

HCID 667475602-(6-Methoxy-quinolin-3-ylsulfanyl)-ethanolYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Mercaptoethanol (0.11 mL, 1.51 mmol, 2.0 eq) is added at room temperature to a stirred solution of 3-bromo-6-methoxy-quinoline (200 mg, 0.76 mmol, 1.0 eq) in N,N-dimethylformamide (10 mL), followed by sodium hydride (50%, 174 mg, 3.78 mol, 5.0 eq). After 4 hours stirring at 80° C., solvent is evaporated and the residue is extracted with ethyl acetate (3×50 mL) and water (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: ethyl acetate:hexane, 1:4 to 1:2, v/v) to afford 2-(6-methoxy-quinolin-3-ylsulfanyl)-ethanol as a yellow viscous oil (140 mg, 79% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with ethyl acetate (3×50 mL) and water (10 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product that
  7. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-9006983ee79f4f0eb842560e933f413b
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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