6-Methoxyquinoline → Quinoline, 1,2,3,4-tetrahydro-6-methoxy-

HRID 219551

Reaktionsgleichung

Reaktionsgleichung von HRID 219551
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7][CH2:6]2

Komponenten

5

Edukt 2

HCID 148606-MethoxyquinolineHCID 2723923Ammonium formate

Produkt 1

HCID 67113Quinoline, 1,2,3,4-tetrahydro-6-methoxy-Ausbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 6-methoxyquinoline (69 μL, 0.5 mmol), ammonium formate (0.32 g, 5.0 mmol), and 10% Pd/C (0.05 g) in anhydrous MeOH (5 mL) was microwaved for 900 s at 100° C. The mixture was filtered and 2M HCl in Et2O (1.5 mL) was added. The product was redissolved in H20/DCM and the aqueous layer basified with 0.1M aq. NaOH (pH 8). After extracting three times with DCM, the organic layer was concentrated to give the product in 89% yield. The product was used without further purification. LC/MS (10-99%) M/Z: M+1 obs=164.0; tR=0.40 min.

Aufarbeitung

  1. customwas microwaved for 900 s at 100° C
  2. filtrationThe mixture was filtered
  3. addition2M HCl in Et2O (1.5 mL) was added
  4. dissolutionThe product was redissolved in H20/DCM
  5. extractionAfter extracting three times with DCM
  6. concentrationthe organic layer was concentrated
  7. customto give the product in 89% yield
  8. customThe product was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-cb92215acb624aeb9d073be02ce94bf4
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202861B2

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