HCID 57447021, compound → HCID 57447017, compound

HRID 2362523Notes

Reaction equation

HRID 2362523 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]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.[H][H]>[Pd].C(O)C>[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]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 2

HCID 57447021HCID 57447021, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57447017HCID 57447017, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A Parr hydrogenation vessel was charged with ethyl 6-(3-nitroquinolin-4-ylamino)hexanoate (14.4 g, 43.2 mmol), 10% palladium on carbon catalyst (1.0 g), and ethanol (250 mL); placed on a Parr shaker; and the system pressurized to 40 psi (2.7×105 Pa) hydrogen. After shaking for 15 hours, the reaction mixture was filtered through CELITE filter agent and concentrated under reduced pressure to provide ethyl 6-(3-aminoquinolin-4-ylamino)hexanoate as a dark oil (9.8 g) that was used directly in the next step without further purification. This step was repeated several times to provide material for the subsequent step.

Workup

  1. filtrationthe reaction mixture was filtered through CELITE
  2. filtrationfilter agent
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-31fda19eea44404289c9ff4ea485e190
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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