Phosphorus oxychloride → HCID 71742712, Verbindung

HRID 1852240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852240
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](O)=[N:8][CH:7]=[C:6]2[N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[C:6]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:7][N:8]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178487756HCID 178487756, Verbindung

Produkt 1

HCID 71742712HCID 71742712, VerbindungAusbeute 18 %

Versuchsvorschrift

A solution of 6-methoxy-4-morpholinoisoquinolin-1-ol (0.33 g, 1.268 mmol) in POCl3 (5 ml) was refluxed for overnight. 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 combine 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 (0.065 g, 18%) as oil. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.18-8.16 (d, J=8 Hz 1H), 7.94 (s, 1H), 7.45-7.40 (m, 2H), 3.98 (s, 3H), 3.88-3.86 (m, 4H), 3.09-3.07 (m, 4H); MS: MS m/z 279.1 (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 combine 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-7001a5b717e44f32bbdf2e156c1b1870
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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