Lawesson's reagent → 6-Pyridin-3-yl-3,4-dihydroquinoline-2(1H)-thione

HRID 44191Notes

Reaction equation

HRID 44191 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=O)[CH2:11][CH2:10]3)[CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[S:27])[CH2:11][CH2:10]3)[CH:2]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 137288626-(Pyridin-3-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 251803006-Pyridin-3-yl-3,4-dihydroquinoline-2(1H)-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6-Pyridin-3-yl-3,4-dihydro-1H-quinolin-2-one (395 mg, 1.76 mmol) and Lawessons reagent (356 mg, 0.88 mmol) was refluxed in 30 ml toluene for 2 h. After evaporation of the solvent under reduced pressure, the residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate, 3/7, Rf=0.31) which gave 6-Pyridin-3-yl-3,4-dihydro-1H-quinoline-2-thione as yellow plates (63 mg, 0.26 mmol, 15%), mp (hexanes/ethyl acetate) 267° C. 1H-NMR (500 MHz, DMSO-d6): δ=2.87 (m, 2H), 2.97 (m, 2H), 7.20 (d, 3J=8.2 Hz, 1H), 7.46 (dd, 3J=7.9 Hz, 3J=4.6 Hz, 1H), 7.59 (dd, 3J=8.2 Hz, 4J=1.9 Hz, 1H), 7.62 (d, 4J=1.9 Hz, 1H), 8.04 (m, 1H), 8.53 (dd, 3J=4.7 Hz, 4J=1.6 Hz, 1H), 8.87 (d, 4J=2.2 Hz, 1H), 12.30 (s, 1H). MS m/z=241.05 (MH+).

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate, 3/7, Rf=0.31) which

Sources & evidence

ORD record
ord-7cfdd5cb9af74adfb11e186ef9badbf0
Source dataset
uspto-grants-2013_09
Patent number
US08541404B2

Reaction notes

Loading…