Phosphorus oxychloride → Methyl 1-chloroisoquinoline-5-carboxylate

HRID 1051273

Reaktionsgleichung

Reaktionsgleichung von HRID 1051273
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N+:9]([O-])=[CH:10]2)=[O:4].O=P(Cl)(Cl)[Cl:18]>ClCCl>[Cl:18][C:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:6]=2[CH:7]=[CH:8][N:9]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 1180908815-(Methoxycarbonyl)isoquinoline 2-oxide

Produkt 1

HCID 72213626Methyl 1-chloroisoquinoline-5-carboxylateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

5-(Methoxycarbonyl)isoquinoline 2-oxide (2 g, 9.84 mmol) obtained in Step (4) of Preparation Example 1 was dissolved in dichloromethane (20 mL), added with POCl3 (20 mL) at room temperature, and stirred for 4 hours or more at 90° C. The temperature of the reaction mixture was lowered to room temperature, followed by quenching with distilled water. The reaction mixture was diluted with dichloromethane, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (1.86 g, 86%).

Aufarbeitung

  1. customwas lowered to room temperature
  2. customby quenching with distilled water
  3. additionThe reaction mixture was diluted with dichloromethane
  4. washwashed with a saturated aqueous sodium bicarbonate solution and saline
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-51f304266d784ea59cc32b001902bdf9
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388165B2

Verknüpfte Notizen

Wird geladen…