Phosphorus oxychloride → 1-Chloro-7-fluoro-4-methoxyisoquinoline

HRID 2361612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361612
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:13][CH3:14])=[CH:7][NH:8][C:9]2=O)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=2)[C:6]([O:13][CH3:14])=[CH:7][N:8]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 222502317-Fluoro-4-methoxyisoquinolin-1-OL

Produkt 1

HCID 222502381-Chloro-7-fluoro-4-methoxyisoquinolineAusbeute 24 %

Versuchsvorschrift

A solution of 7-fluoro-4-methoxyisoquinolin-1(2H)-one (11 g, 56.9 mmol) in POCl3 (100 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 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 (20% ethyl acetate in pet ether) to get desired compound (2.9 g, 24%) as off-white solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.36-8.32 (m, 1H), 7.93-7.90 (m, 1H), 7.88 (s, 1H), 7.70-7.65 (m, 1H), 4.11 (s, 3H); MS: MS m/z 212.1 (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 (20% ethyl acetate in pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-446add8215fc470c84b89013f3dbed66
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691757B2

Notizen zur Reaktion

Wird geladen…