3-[(7-Bromo-3-nitroquinolin-4-yl)amino]propyl acetate → 3-[(3-Amino-7-bromoquinolin-4-yl)amino]propyl acetate

HRID 415528Notes

Reaction equation

HRID 415528 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([Br:19])=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[N+:20]([O-])=O)(=[O:3])[CH3:2]>C(#N)C.[Pt]>[C:1]([O:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([Br:19])=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[NH2:20])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 666202383-[(7-Bromo-3-nitroquinolin-4-yl)amino]propyl acetate

Product 1

HCID 666198733-[(3-Amino-7-bromoquinolin-4-yl)amino]propyl acetateYield 97.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

To a hydrogenation flask was added a solution of 3-[(7-bromo-3-nitroquinolin-4-yl)amino]propyl acetate (60.8 g, 165.1 mmol) in acetonitrile (600 mL) followed by 5% platinum on carbon (6.7 g) and the reaction was hydrogenated at 40 psi (2.8×105 Pa) overnight. The reaction was filtered through CELITE filter aid and the filtrate was collected. The solvent was removed under reduced pressure to afford 3-[(3-amino-7-bromoquinolin-4-yl)amino]propyl acetate (54.6 g) as an oil.

Workup

  1. customwas hydrogenated at 40 psi (2.8×105 Pa) overnight
  2. filtrationThe reaction was filtered through CELITE
  3. filtrationfilter aid
  4. customthe filtrate was collected
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e045b79490e14175afffa2df7821b152
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

Loading…