Phosphorus oxychloride → HCID 22250112, Verbindung

HRID 2361608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361608
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6](=O)[NH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:6]1[C:7]2[C:12](=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[CH:4][N:5]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 222502544,6-Dimethoxy-1(2H)-isoquinolinone

Produkt 1

HCID 22250112HCID 22250112, VerbindungAusbeute 27,5 %

Versuchsvorschrift

A solution of 4,6-dimethoxyisoquinolin-1(2H)-one (4 g, 19.49 mmol) in POCl3 (40 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 by 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 (20% ethyl acetate in pet ether) to get desired compound (1.2 g, 27.5%) as pale yellow solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.16-8.13 (d, J=12 Hz, 1H), 7.74 (s, 1H), 7.44-7.43 (d, J=4 Hz, 1H), 7.30-7.27 (d, J=12 Hz, 1H), 7.26 (s, 1H), 4.05 (s, 3H), 3.97 (s, 3H); MS: MS m/z 224.2 (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 (20% ethyl acetate in pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-282422b133da4dc2b8e94c4130af5bf4
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691757B2

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