HCID 21521307, compound → 1,2,3,4-Tetrahydro-1-methyl-7-propyl-8-quinolinol

HRID 918218Notes

Reaction equation

HRID 918218 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:13][CH2:14][CH3:15])[C:10]=2[OH:12])[CH:5]=[CH:4][CH2:3]1.[H][H]>O.[Ni]>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:13][CH2:14][CH3:15])[C:10]=2[OH:12])[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 21521307HCID 21521307, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 215213081,2,3,4-Tetrahydro-1-methyl-7-propyl-8-quinolinolYield 36%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

Into a stainless steel autoclave, one introduces 37.3 g of paratoluenesulfonate of N-methyl-7-propyl-8-hydroxyquinoline (0.1 mole) in 120 ml of water, and 5 g of Raney nickel. The hydrogenation is carried out under an 80 kg/cm2 hydrogen pressure. After absorption of the hydrogen, one cools and filters off the catalyst; one neutralizes the filtrate with an ammonia solution, resulting in the formation of a grayish-white precipitate that one separates and distills under high vacuum. One collects 8 g of a colorless liquid that distills at 180°-110°C under a 0.5 mm Hg pressure. One obtains a yield of 36%.

Workup

  1. customAfter absorption of the hydrogen, one cools and filters off the catalyst
  2. customresulting in the formation of a grayish-white precipitate that one separates
  3. distillationdistills under high vacuum
  4. distillationthat distills at 180°-110°C under a 0.5 mm Hg pressure
  5. customOne obtains a yield of 36%

Sources & evidence

ORD record
ord-cedce67b48f44ef7ac9bf9e71a18b8cc
Source dataset
uspto-grants-1976_07
Patent number
US03970454

Reaction notes

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