Ammonia → 1-Methyl-1,2,3,4-tetrahydro-8-quinolinol

HRID 918213Notes

Reaction equation

HRID 918213 reaction equation
COS([O-])(=O)=O.[CH3:7][N+:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[OH:18])[CH:11]=[CH:10][CH:9]=1.N>O.[Ni]>[CH3:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[OH:18])[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 1979788-Hydroxy-1-methylquinolinium methyl sulfate

Product 1

HCID 129459811-Methyl-1,2,3,4-tetrahydro-8-quinolinol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

One introduces into a steel autoclave 54.2 g of N-methyl-8-hydroxyquinolinium methylsulfate (i.e. 0.2 mole) in 100 ml of water and 5 g of activated Raney nickel. The hydrogenation is effected under a hydrogen pressure of from 70 to 80 kg/cm2, at a temperature of 80°C. After cooling, one filters off the catalyst and one neutralizes with an ammonia solution. One dries the crystallized product that is formed and one recrystallizes it in methanol.

Workup

  1. customat a temperature of 80°C
  2. temperatureAfter cooling
  3. customis formed
  4. customone recrystallizes it in methanol

Sources & evidence

ORD record
ord-1f8896ee05b14b8b8059337483785b2a
Source dataset
uspto-grants-1976_07
Patent number
US03970454

Reaction notes

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