Propanal → 6-Methoxy-1-propyl-1,2,3,4-tetrahydroquinoline

HRID 1248859

Reaction equation

HRID 1248859 reaction equation
[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.[CH:13](=O)[CH2:14][CH3:15]>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 527PropanalHCID 67113Quinoline, 1,2,3,4-tetrahydro-6-methoxy-

Product 1

HCID 133406506-Methoxy-1-propyl-1,2,3,4-tetrahydroquinolineYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 148.6 g. of 6-methoxy-1,2,3,4-tetrahydroquinoline and 58 g. of propionaldehyde in 275 ml. of ethanol was hydrogenated at 60 psi over 15 g. of 15% palladium on carbon at room temperature for 2 hours and then at 50° C. overnight. The catalyst was removed by filtration and the filtrate concentrated to give a brown oil which was distilled to give 100.5 g. of 6-methoxy-1-n-propyl-1,2,3,4-tetrahydroquinoline (54% yield) as an oil boiling in the range 115°-128° C. at 0.02 Torr.

Workup

  1. customat 50° C.
  2. customovernight
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate concentrated
  5. customto give a brown oil which
  6. distillationwas distilled
  7. customto give 100.5 g

Sources & evidence

ORD record
ord-7b73e8318785455d87d8509c6c15fc37
Source dataset
uspto-grants-1986_12
Patent number
US04626591

Linked notes

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