Phosphorus oxychloride → 1-Chloro-4-methylisoquinoline

HRID 1852211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852211
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N+:4]([O-])[CH:3]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([CH3:1])=[CH:3][N:4]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 229588294-Methylisoquinoline 2-oxide

Produkt 1

HCID 222502291-Chloro-4-methylisoquinolineAusbeute 18,75 %

Versuchsvorschrift

A solution of 4-methylisoquinoline 2-oxide (0.65 g, 4.08 mmol) in POCl3 (6 ml) was refluxed for 18 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified with solid sodium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (10% ethyl acetate in pet ether) to get desired compound (0.17 g, 18.75%) as oil. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.14-8.12 (d, J=8 Hz, 1H), 7.97 (s, 1H), 7.95-7.93 (d, J=8 Hz, 1H), 7.86 (t, J=4 Hz, 1H), 7.84(t, J=8 Hz, 1H), 2.59 (s, 3H); MS: MS m/z 178.2 (M++1).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with cold water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto get crude compound
  8. customThe crude compound was purified by silica gel chromatography (10% ethyl acetate in pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-2e033a9ccd0442bc90b915fc9e3bd29f
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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