Benzoyl chloride → N-benzoyl-2-cyano-3-methyl-1,2-dihydroquinoline

HRID 52514

Reaktionsgleichung

Reaktionsgleichung von HRID 52514
[C-:1]#[N:2].[K+].[CH3:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.ClCCl>[C:15]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[C:5]([CH3:4])[CH:6]1[C:1]#[N:2])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 7412Benzoyl chlorideHCID 9032Potassium CyanideHCID 119263-Methylquinoline

Produkt 1

HCID 19963227N-benzoyl-2-cyano-3-methyl-1,2-dihydroquinolineAusbeute 108 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of potassium cyanide (68.22 g, 1.048 mol), and 3-methylquinoline (50 g, 0.349 mol) in water (200 mL) and dichloromethane (500 mL) was added dropwise benzoyl chloride (81 mL, 0.698 mol) over 2 h at room temperature. The mixture was stirred for 4.5 h at room temperature and then the organic layer was separated. The layer was washed successively with water (300 mL), 1N aqueous hydrochloric acid, and water (200 mL×2), dried over magnesium sulfate, and concentrated to give 103.05 g of N-benzoyl-2-cyano-3-methyl-1,2-dihydroquinoline (108%): 1H NMR (270 MHz, CDCl3) δ7.34 (m, 6H), 7.16 (dd, 1H, J=7.6, 1.3 Hz), 7.07 (dt, 1H, J=1.3, 7.6 Hz), 6.87 (dt, 1H, J=1.3, 7.6 Hz), 6.53 (dd, 1H, J=7.6, 1.3 Hz), 2.12 (d, 3H, J=1.3 Hz).

Aufarbeitung

  1. customthe organic layer was separated
  2. washThe layer was washed successively with water (300 mL), 1N aqueous hydrochloric acid, and water (200 mL×2)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ad69b5c1a3df461c89baa0ea0a731f6e
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616586

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