Ethanol → 4-[(3-Aminoquinolin-4-yl)amino]butan-1-ol

HRID 2404991Notes

Reaction equation

HRID 2404991 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.[H][H].C(O)C>C1(C)C=CC=CC=1.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

6

Reactant 3

HCID 702EthanolHCID 121061814-[(3-Nitroquinolin-4-yl)amino]butan-1-olHCID 178418361HCID 178418361, compound2×

Product 1

HCID 689990994-[(3-Aminoquinolin-4-yl)amino]butan-1-olYield 105.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

Catalyst (5% Pd/C) was added to a suspension of 4-[(3-nitroquinolin-4-yl)amino]butan-1-ol (18.2 g, 69.6 mmol) in toluene (450 mL) in a Parr vessel. The vessel was placed on a shaker and pressurized with hydrogen. The next day ethanol (60 mL) and additional catalyst were added and the vessel was again pressurized with hydrogen. After 1 hour analysis by TLC indicated that all of the starting material had been consumed. The reaction mixture was filtered through a layer of CELITE filter aid and then concentrated under reduced pressure to provide 17 g of 4-[(3-aminoquinolin-4-yl)amino]butan-1-ol.

Workup

  1. customthat all of the starting material had been consumed
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-812bdfd837d643e3bdc2e52534ef5f24
Source dataset
uspto-grants-2014_08
Patent number
US08802853B2

Reaction notes

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