tert-Butyl (2S)-2-[(3-nitroquinolin-4-yl)amino]propylcarbamate → tert-butyl (2S)-2-[(3-aminoquinolin-4-yl)amino]propylcarbamate

HRID 549126Notes

Reaction equation

HRID 549126 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C@@H:15]([CH3:25])[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>C(#N)C.[Pt]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C@@H:15]([CH3:25])[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 86624122tert-Butyl (2S)-2-[(3-nitroquinolin-4-yl)amino]propylcarbamate

Product 1

HCID 86624121tert-butyl (2S)-2-[(3-aminoquinolin-4-yl)amino]propylcarbamateYield 100.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

tert-Butyl (2S)-2-[(3-nitroquinolin-4-yl)amino]propylcarbamate (5.04 g, 14.5 mmol) was dissolved in acetonitrile (300 mL) and the solution was placed in a pressure bottle. Platinum on carbon (5%, 1.03 g) was then added and the reaction mixture was shaken under H2 at 30 PSI (2.1×105 Pa). After 20 hours, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with acetonitrile and the combined filtrates were concentrated under reduced pressure to give tert-butyl (2S)-2-[(3-aminoquinolin-4-yl)amino]propylcarbamate (4.60 g) as an orange foam.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with acetonitrile
  4. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-db387fa251f244188ea4bb9a69971b58
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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