HCID 66620230, compound → HCID 66620332, compound

HRID 1364050Notes

Reaction equation

HRID 1364050 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1>ClCCl.C(OCC)(=O)C.[Pt]>[NH2:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=2

Participants

5

Reactant 1

HCID 66620230HCID 66620230, compound

Product 1

HCID 66620332HCID 66620332, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 3-[(7-bromo-3-nitroquinolin-4-yl)amino]propylcarbamate (56.4 g, 133 mmol) in dichloromethane (150 mL) and ethyl acetate (500 mL) and 5% platinum on carbon (15.52 g, 79.56 mmol) were added to a hydrogenation vessel, which was placed under hydrogen pressure (50 psi, 3.4×105 Pa) and shaken overnight. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was dried under reduced pressure to provide 52.17 g of tert-butyl 3-[(3-amino-7-bromoquinolin-4-yl)amino]propylcarbamate.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-ea9d3d8fb9244c0aa354f86972fb0902
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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