Dichloromethane methanol → Methyl 5-aminoisoquinoline-3-carboxylate

HRID 1791303

Reaktionsgleichung

Reaktionsgleichung von HRID 1791303
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:14]([O:16][CH3:17])=[O:15])[N:8]=[CH:9]2)([O-])=O.CO.C(Cl)Cl>C(O)(=O)C.O.[Fe]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:14]([O:16][CH3:17])=[O:15])[N:8]=[CH:9]2

Komponenten

5

Edukt 2

HCID 21226129Dichloromethane methanolHCID 22032663Methyl 5-nitroisoquinoline-3-carboxylate

Produkt 1

HCID 22032628Methyl 5-aminoisoquinoline-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 21899381Acetic acid--water (1/1)Lösungsmittel

Versuchsvorschrift

The product of Example 71A (10.33 g, 44.5 mmol) in acetic acid/water (3/1) (320 mL) was treated with iron powder (5.06 g, 90.7 mmol). After stirring for 16 hours at room temperature, the reaction mixture was filtered the filtrate concentrated under reduced pressure to approximately half the original volume. The mixture was then extracted with dichloromethane (3×200 mL). The organic fractions were combined, dried (MgSO4), and the filtrate concentrated under reduced pressure to afford crude material. A precipitate formed in the aqueous phase after sitting for several hours. This was filtered to afford additional crude material. The crude material was purfidied by column chromatography (2% methanol/CH2Cl2) to provide the title compound. MS (ESI+) m/z 203 (M+H)+; MS (ESI−) m/z 201 (M−H)−; 1H NMR (DMSO-d6, 300 MHz) δ 3.92 (s, 3H), 6.34 (s, 2H), 6.96 (dd, J 1.0, 7.8, 1H), 7.31 (d, J 8.1, 1H), 7.51 (t, J 7.9, 1H), 8.82 (s, 1H), 9.15 (s, 1H); Anal. Calcd for C11H10N2O2: C, 65.34; H, 4.99; N, 13.85. Found: C, 65.03; H, 4.95; N, 13.65.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered the filtrate
  2. concentrationconcentrated under reduced pressure to approximately half the original volume
  3. extractionThe mixture was then extracted with dichloromethane (3×200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto afford crude material
  7. customA precipitate formed in the aqueous phase
  8. waitafter sitting for several hours
  9. filtrationThis was filtered
  10. customto afford additional crude material

Quellen und Nachweise

ORD-Eintrag
ord-01fb787146f347a1af791d906562fe79
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074805B2

Verknüpfte Notizen

Wird geladen…