(7-Bromo-3-nitroquinolin-4-yl)isobutylamine → 7-bromo-N4-isobutylquinoline-3,4-diamine

HRID 1818212Notes

Reaction equation

HRID 1818212 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.[Pt]>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 21984282(7-Bromo-3-nitroquinolin-4-yl)isobutylamine

Product 1

HCID 688181597-bromo-N4-isobutylquinoline-3,4-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent2×

Procedure

(7-Bromo-3-nitroquinolin-4-yl)-(2-methylpropyl)amine (117 g) was dissolved in hot toluene (2 L) and poured into stainless steel Parr vessel. Additional toluene (2 L) and 5% platinum on carbon (12.5 g) were added. The vessel was evacuated, charged with hydrogen (54 psi, 3.7×105 Pa), and shaken overnight at room temperature. The reaction mixture evacuated, filtered through a layer of CELITE filter aid, and concentrated under reduced pressure to provide 7-bromo-N4-(2-methylpropyl)quinoline-3,4-diamine, which was used without purification.

Workup

  1. customThe vessel was evacuated
  2. additioncharged with hydrogen (54 psi, 3.7×105 Pa)
  3. customThe reaction mixture evacuated
  4. filtrationfiltered through a layer of CELITE
  5. filtrationfilter aid
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8503d0b372b3451eab074e3394a196e3
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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