6-Hydroxymethylquinoline → 1,2,3,4-Tetrahydroquinolin-6-ylmethanol

HRID 279238

Reaktionsgleichung

Reaktionsgleichung von HRID 279238
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2>O.[Pt](=O)=O.CO>[OH:1][CH2:2][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

4

Edukt 1

HCID 15143856-Hydroxymethylquinoline

Produkt 1

HCID 226628871,2,3,4-Tetrahydroquinolin-6-ylmethanolAusbeute 68,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11139377Platinum dioxide monohydrateKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

6-Hydroxymethylquinoline (1 g, 6.28 mmoles) (prepared by the method of: C. E. Kaslow and W. R. Clark, J. Org. Chem., 1953, 18, 55-58.) and methanol (200 mL) were placed in a Parr bomb and platinum (IV) oxide monohydrate (0.5 g, 2.04 mmoles) was added. The mixture was hydrogenated at 50 psi at 25° C. for 2 h. The catalyst was filtered off and washed with methanol. The combined filtrates were evaporated to dryness and the product was chromatographed on silica gel using 1.5% (10% conc. NH4OH in methanol)dichloromethane as the eluant to give the title compound (0.7044 g, 68%): CIMS: m/z 164.35 (MH+); δH (CDCl3) 1.93 (2H, m, 3-CH2) and 2.76 (2H, t, 4-CH2), 3.30 (2H, m, 2-CH2), 4.50 (2H, s, CH2OH), 6.45 (1H, d, Ar—H8), 6.96 ppm (2H, m, Ar—H5 and Ar—H7); δC (CDCl3) CH2: 22.1, 27.0, 42.0, 65.6; CH: 114.2, 126.4, 129.2; C: 121.5, 129.4, 144.5.

Aufarbeitung

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. washwashed with methanol
  4. customThe combined filtrates were evaporated to dryness
  5. customthe product was chromatographed on silica gel using 1.5% (10% conc. NH4OH in methanol)dichloromethane as the eluant

Quellen und Nachweise

ORD-Eintrag
ord-98935e77f2184c0ebc2b9efb39883832
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362188B1

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