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

HRID 1840839Notes

Reaction equation

HRID 1840839 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[CH:18][C:17]=1[N+:26]([O-])=O)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]>C1(C)C=CC=CC=1.[Pt]>[NH2:26][C:17]1[CH:18]=[N:19][C:20]2[C:25]([C:16]=1[NH:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])=[CH:24][CH:23]=[CH:22][CH:21]=2

Participants

4

Reactant 1

HCID 69010146Tert-butyl methyl(2-(2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethyl)carbamate

Product 1

HCID 69011088Tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethyl(methyl)carbamateYield 112.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

A solution of tert-butyl methyl(2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethyl)carbamate (6.56 g, 16.8 mmol) in 75 mL of toluene was treated with 0.5 g of 5% Pt on carbon and shaken under H2 (3 Kg/cm2) for 24 h. The solution was then filtered through a Celite pad and concentrated to give 6.8 g of crude tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethyl(methyl)carbamate as an orange syrup which was carried on without further purification.

Workup

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

Sources & evidence

ORD record
ord-6aba1ae176e04c42ae9c3fd6aa70c7f9
Source dataset
uspto-grants-2004_01
Patent number
US06683088B2

Reaction notes

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