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

HRID 392509

Reaktionsgleichung

Reaktionsgleichung von HRID 392509
[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.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 178526985HCID 178526985, VerbindungKatalysatorHCID 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 (I) 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+); 6. (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-4911dadd12734abea3873a12af6614c1
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800636B2

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