Tert-butyl 2-[(2-chloro-3-nitroquinolin-4-yl)amino]ethylcarbamate → Tert-butyl 2-[(3-amino-2-chloroquinolin-4-yl)amino]ethylcarbamate

HRID 1097598Notes

Reaction equation

HRID 1097598 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>[Pt].C(#N)C>[NH2:12][C:11]1[C:2]([Cl:1])=[N:3][C:4]2[C:9]([C:10]=1[NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 86616881Tert-butyl 2-[(2-chloro-3-nitroquinolin-4-yl)amino]ethylcarbamate

Product 1

HCID 86616882Tert-butyl 2-[(3-amino-2-chloroquinolin-4-yl)amino]ethylcarbamateYield 104.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

Platinum on carbon (1.5 g of 5%) was added to a solution of tert-butyl 2-[(2-chloro-3-nitroquinolin-4-yl)amino]ethylcarbamate (13.99 g, 38.19 mmol) in acetonitrile (100 mL) in a Parr vessel. The mixture was placed under hydrogen pressure (30 psi, 2.1×105 Pa) for three hours and then filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure and further dried overnight on a vacuum pump to provide 13.46 g of tert-butyl 2-[(3-amino-2-chloroquinolin-4-yl)amino]ethylcarbamate as a light brown solid.

Workup

  1. customfor three hours
  2. filtrationfiltered through a layer of CELITE filter agent
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customfurther dried overnight on a vacuum pump

Sources & evidence

ORD record
ord-0d6db6d8c66745e39e831ad22a68b588
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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