7-Methoxyquinoline → 7-Methoxy-1,2,3,4-tetrahydroquinoline

HRID 1520178Notes

Reaction equation

HRID 1520178 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1>CO.O=[Pt]=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][NH:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 786667-Methoxyquinoline

Product 1

HCID 162443887-Methoxy-1,2,3,4-tetrahydroquinolineYield 73.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7-methoxyquinoline (2.0 g, 12.56 mmol) in methanol (60 ml) was added PtO2 (180 mg, 0.79 mmol). H2 (g) was introduced into above solution and the reaction was stirred overnight at room temperature and then the solids were filtered off. The organics were concentrated in vacuo to give a residue, which was purified by silica gel column chromatography with 3% ethyl acetate in petroleum ether to afford 7-methoxy-1,2,3,4-tetrahydroquinoline as a light yellow oil (1.5 g, 73%).

Workup

  1. additionH2 (g) was introduced into above solution
  2. filtrationthe solids were filtered off
  3. concentrationThe organics were concentrated in vacuo
  4. customto give a residue, which
  5. customwas purified by silica gel column chromatography with 3% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-762f89ecda7745aba699fc390fd16151
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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