6-(3-Nitroquinolin-4-ylamino)-1-phenylhexan-1-one → 6-(3-Aminoquinolin-4-ylamino)-1-phenylhexan-1-one

HRID 521271Notes

Reaction equation

HRID 521271 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>[Pt].C1(C)C=CC=CC=1>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 688765506-(3-Nitroquinolin-4-ylamino)-1-phenylhexan-1-one

Product 1

HCID 689281276-(3-Aminoquinolin-4-ylamino)-1-phenylhexan-1-oneYield 100.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 6-(3-nitroquinolin-4-ylamino)-1-phenylhexan-1-one (2.27 g, 6.25 mmol) and 5% platinum on carbon catalyst (0.50 g) in toluene (60 mL) was hydrogenated on a Parr shaker at 50 psi (3.4×105 Pa) for 3 hours. After filtration through CELITE filter agent and concentration under reduced pressure, 6-(3-aminoquinolin-4-ylamino)-1-phenylhexan-1-one (2.09 g) was obtained as a dark yellow oil that was used directly in the next step without further purification.

Workup

  1. filtrationAfter filtration through CELITE
  2. filtrationfilter
  3. concentrationagent and concentration under reduced pressure

Sources & evidence

ORD record
ord-da86c6cd091c4937b9ea3cfc97ce47b6
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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