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

HRID 279238

Reaction equation

HRID 279238 reaction equation
[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

Participants

4

Reactant 1

HCID 15143856-Hydroxymethylquinoline

Product 1

HCID 226628871,2,3,4-Tetrahydroquinolin-6-ylmethanolYield 68.7%

Reagents, catalysts & solvents 2

HCID 11139377Platinum dioxide monohydrateCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-98935e77f2184c0ebc2b9efb39883832
Source dataset
uspto-grants-2002_03
Patent number
US06362188B1

Linked notes

Loading…