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

HRID 1440696Notes

Reaction equation

HRID 1440696 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C(O)C.[Na]>O>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH2:9][CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 702EthanolHCID 113598-AminoquinolineHCID 5360545Sodium2×

Product 1

HCID 1046728-Quinolinamine, 1,2,3,4-tetrahydro-Yield 52.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 20.00 g of 8-aminoquinoline in boiling absolute ethanol (400 ml) was added 44.74 g of sodium pellets over 20 mins, with stirring, until the sodium is dissolved. The reaction mixture was poured into water (50 ml) and concentrated. The residue was diluted with sodium bicarbonate solution and the mixture was extracted with dichloromethane. The extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated. The residue was distilled under vacuum to give 10.77 g (52.3%) of product.

Workup

  1. dissolutionis dissolved
  2. concentrationconcentrated
  3. additionThe residue was diluted with sodium bicarbonate solution
  4. extractionthe mixture was extracted with dichloromethane
  5. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated
  8. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-37823c2598244c419614f9098d6e3b70
Source dataset
uspto-grants-1996_03
Patent number
US05500423

Reaction notes

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