Isopropanol → N4-(2-amino-2-methylpropyl)quinoline-3,4-diamine

HRID 353909Notes

Reaction equation

HRID 353909 reaction equation
[CH3:1][C:2]([NH2:19])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[N+:15]([O-])=O.C(O)(C)C>C1(C)C=CC=CC=1.[Pt]>[NH2:19][C:2]([CH3:18])([CH3:1])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15]

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 590266622-methyl-N1-(3-nitroquinolin-4-yl)propane-1,2-diamine

Product 1

HCID 85850670N4-(2-amino-2-methylpropyl)quinoline-3,4-diamineYield 100%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

A solution of 2-methyl-N1-(3-nitroquinolin-4-yl)propane-1,2-diamine (2.45 g, 9.42 mmol), in 100 mL of toluene and 50 mL of isopropanol was treated with 0.5 g of 5% Pt on carbon and shaken under H2 (3 atm, 3 Kg/cm2) for 3 h. The solution was then filtered through a Celite pad and concentrated to give 2.17 g of crude N4-(2-amino-2-methylpropyl)quinoline-3,4-diamine as a light brown foam.

Workup

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

Sources & evidence

ORD record
ord-f59ff8aff79547578195428c9165d5ca
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Reaction notes

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