Thioanisole → 2-[(heptylsulfanyl)methyl]-3-methylquinolin-4(1H)-one

HRID 384489Notes

Reaction equation

HRID 384489 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][S:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:10]=1[CH3:28])C1C=CC=CC=1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH2:21]([S:20][CH2:19][C:11]1[NH:12][C:13]2[C:18]([C:9](=[O:8])[C:10]=1[CH3:28])=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 595272964-(Benzyloxy)-2-[(heptylsulfanyl)methyl]-3-methylquinoline

Product 1

HCID 595272552-[(heptylsulfanyl)methyl]-3-methylquinolin-4(1H)-oneYield 95.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 4-(benzyloxy)-2-[(heptylsulfanyl)methyl]-3-methylquinoline (150 mg) in trifluoroacetic acid (5 mL) was added thioanisole (150 mg), followed by stirring at room temperature for 16 hours. The reaction mixture was added dropwise to an ice-cold aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate (50 mL). The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1) to obtain 2-[(heptylsulfanyl)methyl]-3-methylquinolin-4(1H)-one (110 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate (50 mL)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-7d10b21b5f264ec59469e3058e13c6d9
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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