HCID 66958491, compound → HCID 66958404, compound

HRID 1364033Notes

Reaction equation

HRID 1364033 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][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>ClCCCl.[Pt]>[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][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 66958491HCID 66958491, compound

Product 1

HCID 66958404HCID 66958404, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of tert-butyl 3-[(3-nitroquinolin-4-yl)amino]propylcarbamate (50.0 g, 144 mmol) in 1,2-dichloroethane (450 mL) and 5% platinum on carbon (16.9 g, 86.6 mmol) were added to a Parr vessel, which was placed under hydrogen pressure (30 psi, 2.1×105 Pa) and shaken until the reaction was complete. The reaction mixture was filtered and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the resulting solution was filtered to remove an insoluble impurity, washed sequentially with brine (3×) and dilute aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 42.52 g of tert-butyl 3-[(3-aminoquinolin-4-yl)amino]propylcarbamate.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationthe resulting solution was filtered
  5. customto remove an insoluble impurity
  6. washwashed sequentially with brine (3×) and dilute aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-25b864217a0d4d149f5398ffd79bb8de
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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