Phosphorus oxychloride → 4-Chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile

HRID 970466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970466
C1([NH:7][C:8]([C:10]2[C:11](=[O:22])[N:12]([CH3:21])[C:13]3[C:18]([C:19]=2O)=[CH:17][CH:16]=[CH:15][CH:14]=3)=O)CCCCC1.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH3:21])[C:11](=[O:22])[C:10]=1[C:8]#[N:7]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 54685659N-cyclohexyl-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

Produkt 1

HCID 27857484-Chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbonitrileAusbeute 82 %

Versuchsvorschrift

A solution of Compound 2 (1.5 g, 5 mmol) in 20 mL phosphorus oxychloride was heated at 90° C. for 2 h. The solvent was evaporated under reduced pressure. The residue was suspended in ice water and neutralized by solid sodium bicarbonate. The solids formed were filtered, washed by water, and purified by flash chromatography eluting with 1% methanol in dichloromethane to yield 903 mg (82%) of white solids. M.P. 235° C. 1H NMR (DMSO-d6): 3.66 (s, 3H), 7.50 (t, J=7.7 Hz, 1H), 7.74 (d, J=8.6 Hz, 1H), 7.91 (t, J=8.7 Hz, 1H), 8.08 (d, J=7.6 Hz, 1H). EIMS m/z 219 (M+1), 241 (M+23). Anal. (C17H7ClN2O) C, H, N.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by water
  5. custompurified by flash chromatography
  6. washeluting with 1% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-05b8263375ed496394ed1e76d9b5d4c1
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312220B2

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