(7-Bromo-3-nitroquinolin-4-yl)-(3-isopropoxypropyl)amine → 7-bromo-N4-(3-isopropoxypropyl)quinoline-3,4-diamine

HRID 244808

Reaction equation

HRID 244808 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH2:17][CH2:18][O:19][CH:20]([CH3:22])[CH3:21])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1>C(#N)C.[Pt]>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH2:17][CH2:18][O:19][CH:20]([CH3:22])[CH3:21])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67382099(7-Bromo-3-nitroquinolin-4-yl)-(3-isopropoxypropyl)amine

Product 1

HCID 690787337-bromo-N4-(3-isopropoxypropyl)quinoline-3,4-diamineYield 96.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

(7-Bromo-3-nitroquinolin-4-yl)-(3-isopropoxypropyl)amine (51 g) was slurried in acetonitrile (750 mL) and added to a Parr flask containing 5% platinum on carbon (5 g). The flask was degassed three times, then charged with hydrogen (30 psi) and shaken for 4 hours with replenishment of the hydrogen as necessary. The platinum catalyst was removed by filtration through a bed of CELITE filter agent. The filtrate was evaporated to afford 7-bromo-N4-(3-isopropoxypropyl)quinoline-3,4-diamine as a yellow oil (45 g).

Workup

  1. additionadded to a Parr flask
  2. customThe flask was degassed three times
  3. additioncharged with hydrogen (30 psi)
  4. customThe platinum catalyst was removed by filtration through a bed of CELITE
  5. filtrationfilter agent
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-e3299dfc680b4bdda48ce7a691077feb
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Linked notes

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