Quinolin-8-ylmethanol → (1,2,3,4-Tetrahydroquinolin-8-yl)methanol

HRID 1088788Notes

Reaction equation

HRID 1088788 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2>CO.[Pt]=O>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][CH2:10][CH2:9][CH2:8]2

Participants

4

Reactant 1

HCID 594412Quinolin-8-ylmethanol

Product 1

HCID 14072927(1,2,3,4-Tetrahydroquinolin-8-yl)methanolYield 97.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

8-Hydroxymethylquinoline (1.0 g) was dissolved in methanol (30 ml). Platinum oxide (0.25 g) was added thereto and the mixture was subjected to catalytic reduction at 3.5 kg/cm2, 40° C. After completion of the catalytic reduction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate-n-hexane to give 8-hydroxymethyl-1,2,3,4-tetrahydroquinoline (1.0 g). Yellow needle crystals mp: 67°-68° C.

Workup

  1. customwas subjected to catalytic reduction at 3.5 kg/cm2, 40° C
  2. filtrationAfter completion of the catalytic reduction, the catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-af9b5232f86d4c20a70a6375daf7eb46
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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