6-(Bromomethyl)-1-methylquinolin-2(1H)-one → 1,2,3,4-Tetrahydroquinoline

HRID 1068827Notes

Reaction equation

HRID 1068827 reaction equation
BrC[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9](C)[C:8](=O)[CH:7]=[CH:6]2.[H][H]>O=[Pt]=O>[NH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 151990656-(Bromomethyl)-1-methylquinolin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 694601,2,3,4-Tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

The alkylation step was carried out using 6-bromomethyl-1-methyl-2-oxo-1,2-dihydroquinoline, as in Example 1, and the intermediate was reduced with hydrogen over an Adam's catalyst to give 1,2,3,4-tetrahydroquinoline intermediate which was then deprotected as in Example 13. This provided the title compound as a white solid.

Sources & evidence

ORD record
ord-c42f90e8facf4c51a49e397944392be0
Source dataset
uspto-grants-2001_06
Patent number
US06251913B1

Reaction notes

Loading…