tert-Butyl (4-((3-nitroquinolin-4-yl)amino)butyl)carbamate → tert-Butyl (4-((3-aminoquinolin-4-yl)amino)butyl)carbamate

HRID 895785Notes

Reaction equation

HRID 895785 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][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>[Pt].C1(C)C=CC=CC=1>[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][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 22381766tert-Butyl (4-((3-nitroquinolin-4-yl)amino)butyl)carbamate

Product 1

HCID 18783942tert-Butyl (4-((3-aminoquinolin-4-yl)amino)butyl)carbamateYield 91.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

Platinum on carbon (3.6 g of 5%) was added to a solution of 1,1-dimethylethyl N-{4[(3-nitroquinolin4-yl)amino]butyl}carbamate (36.1 g, 100 mmol) in toluene (1.5 L). The mixture was hydrogenated at 50 psi (3.5 Kg/cm2) for 3 hours. The reaction mixture was filtered through a layer of Celite® filter aid to remove the catalyst. The filtrate was concentrated under vacuum to provide 30.1 g of crude 1,1-dimethylethyl N-{4-[(3-aminoquinolin-4-yl)amino]butyl}carbamate as a gooey orange syrup.

Workup

  1. filtrationThe reaction mixture was filtered through a layer of Celite®
  2. filtrationfilter aid
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-e97df611eb02489ca8a558e33cbd157c
Source dataset
uspto-grants-2005_07
Patent number
US06916925B1

Reaction notes

Loading…