6-Methoxyquinoline → Quinoline, 1,2,3,4-tetrahydro-6-methoxy-

HRID 1719602Notes

Reaction equation

HRID 1719602 reaction equation
[CH3:1][O: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>CO.[Pt](=O)=O>[CH3:1][O: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 148606-Methoxyquinoline

Product 1

HCID 67113Quinoline, 1,2,3,4-tetrahydro-6-methoxy-Yield 66%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of 218.5 g. of 6-methoxyquinoline in 1750 ml of methanol was hydrogenated at 60 psi over 30 g. of platinum dioxide at 50° overnight. The reaction was filtered and the filtrate concentrated to give an oil. The oil was distilled to give 148.6 g. of 6-methoxy-1,2,3,4-tetrahydroquinoline (66% yield) boiling in the range 123°-125° C. at 8 Torr.

Workup

  1. customat 50°
  2. customovernight
  3. filtrationThe reaction was filtered
  4. concentrationthe filtrate concentrated
  5. customto give an oil
  6. distillationThe oil was distilled
  7. customto give 148.6 g

Sources & evidence

ORD record
ord-4f3a640184c44f07a7eea89b6add56f2
Source dataset
uspto-grants-1985_09
Patent number
US04540787

Reaction notes

Loading…