8-Aminoquinoline → 8-Quinolinamine, 1,2,3,4-tetrahydro-

HRID 1082043Notes

Reaction equation

HRID 1082043 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH2:11])[CH:4]=[CH:3][CH:2]=1.[Na]>C(O)C>[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH2:11])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 5360545Sodium2×

Product 1

HCID 1046728-Quinolinamine, 1,2,3,4-tetrahydro-Yield 139.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

25 g (0.169 mol) of quinolin-8-amine are dissolved in 600 ml of ethanol. The reaction mixture is heated to 70° C. and 45 g of sodium are added in small pieces. The mixture is brought to the reflux temperature until the sodium has disappeared. The mixture is then evaporated to dryness and the residue is taken up in an ether/hexane (50/50) mixture, filtered and again evaporated to dryness. 35 g of product are obtained in the form of an oil which is used as is in the following stage.

Workup

  1. customThe mixture is then evaporated to dryness
  2. filtrationfiltered
  3. customagain evaporated to dryness

Sources & evidence

ORD record
ord-e092be8a57a24128843ffd69d114cd3a
Source dataset
uspto-grants-1996_12
Patent number
US05589476

Reaction notes

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