HCID 15224449, compound → HCID 15224450, compound

HRID 396992Notes

Reaction equation

HRID 396992 reaction equation
[CH2:1]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([Cl:16])[C:7]=1[N+:17]([O-])=O)[CH2:2][CH2:3][CH3:4]>[Pt].C1(C)C=CC=CC=1>[NH2:17][C:7]1[C:8]([Cl:16])=[N:9][C:10]2[C:15]([C:6]=1[NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

4

Reactant 1

HCID 15224449HCID 15224449, compound

Product 1

HCID 15224450HCID 15224450, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

4-Butylamino-2-chloro-3-nitroquinoline (33 g, 0.12 mole, Example 112) was combined with toluene (200 mL) and 5% platinum on carbon (1 g). The mixture was hydrogenated on a Parr apparatus at an initial pressure of 38 psi (2.7 Kg/cm2). When the hydrogenation was complete, the catalyst was removed by filtration and the filtrate was concentrated to provide a brown liquid. The liquid was chilled in an ice bath to provide an orange solid. The solid was collected by filtration, slurried with diethyl ether for 30 minutes then filtered to provide 20 g of the desired product as a tan solid. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customto provide a brown liquid
  4. temperatureThe liquid was chilled in an ice bath
  5. customto provide an orange solid
  6. filtrationThe solid was collected by filtration
  7. filtrationthen filtered

Sources & evidence

ORD record
ord-bd71339d06ed41fe8b8028b9a739f597
Source dataset
uspto-grants-2003_08
Patent number
US06608201B2

Reaction notes

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