Tert-butyl 2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethylcarbamate → Tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy)ethylcarbamate

HRID 32374Notes

Reaction equation

HRID 32374 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][O:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>C1(C)C=CC=CC=1.[Pt]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 12106199Tert-butyl 2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethylcarbamate

Product 1

HCID 12106200Tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy)ethylcarbamateYield 99.9%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

A solution of tert-butyl 2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethylcarbamate (7.52 g, 20.0 mmol) in toluene was treated with 1.5 g of 5% Pt on carbon and shaken under H2 (3 Kg/cm2) for 24 hours. The solution was then filtered through a Celite pad and concentrated to give 6.92 g of crude tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate as a yellow syrup.

Workup

  1. filtrationThe solution was then filtered through a Celite pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f26995eb730e482fa12c3dc4a8cc1a39
Source dataset
uspto-grants-2008_09
Patent number
US07427629B2

Reaction notes

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