Piperidine → 2-[2-[(phenylmethyl)thio]-3-pyridinyl]-4(1H)-quinolinone

HRID 275319Notes

Reaction equation

HRID 275319 reaction equation
[C:1]1([CH2:7][S:8][C:9]2[C:14]([CH:15]=O)=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24](=[O:29])[CH2:25]S(C)=O.N1CCCCC1>C1(C)C=CC=CC=1>[C:1]1([CH2:7][S:8][C:9]2[C:14]([C:15]3[NH:17][C:18]4[C:19]([C:24](=[O:29])[CH:25]=3)=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 45319152-(Benzylsulfanyl)nicotinaldehydeHCID 143584271-(2-Aminophenyl)-2-(methylsulfinyl)ethanone

Product 1

HCID 200878972-[2-[(phenylmethyl)thio]-3-pyridinyl]-4(1H)-quinolinoneYield 26.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-[(Phenylmethyl)thio]pyridine-3-carboxaldehyde (6.01 g, 26.2 mmole, 1 equiv.), 1-(2-aminophenyl)-2-(methylsulfinyl)ethanone (5.17 g, 26.2 mmole, 1 equiv.), and piperidine (1.3 ml, 13.1 mmole, 0.5 equiv.) were combined in toluene (240 ml), and the mixture was heated to reflux under a Dean-Stark trap. After 3.5 hr, the reaction was concentrated to one half volume and cooled in the refrigerator overnight. Filtration of the mixture gave 2-[2-[(phenylmethyl)thio]-3-pyridinyl]-4 (1H)-quinolinone (2.37 g, 26%) as a pale yellow solid: mp 219-226 (dec); TLC (50% EtOAc/CHCl3) Rf 0.19; 1H NMR (DMSO-d6) δ11.93 (br s, 1H), 8.67 (dd, J=4.8, 1.8 Hz, 1H), 8.10 (dd, J=8.1, 1.1 Hz, 1H), 7.87 (dd, J=7.7, 1.8 Hz, 1H), 7.60-7.72 (m, 1H), 7.58 (d, J=8.0 Hz, 1H), 7.17-7.45 (m, 7H), 6.06 (br s, 1H), 4.44 (s, 2H); IR (KBr) 2100-3300 (br), 1633, 1595, 1573, 1549, 1534, 1502, 1474, 1440 cm-1 ; MS (NH3), m/e (%) 345.0 (100, (M+H)+), 255.1 (22.7), 253.1 (20.7). Anal. Calcd for C21H16N2OS: C, 73.23; H, 4.68; N, 8.13; S, 9.31. Found: C, 72.98; H, 4.56; N, 8.03; S, 9.20.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under a Dean-Stark trap
  3. concentrationthe reaction was concentrated to one half volume
  4. temperaturecooled in the refrigerator overnight
  5. filtrationFiltration of the mixture

Sources & evidence

ORD record
ord-7afe653e3bd84d3aab04cdcd8625e9e3
Source dataset
uspto-grants-1995_02
Patent number
US05393756

Reaction notes

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