Ethyl 3-[(3-nitroquinolin-4-yl)amino]butanoate → Ethyl 3-[(3-aminoquinolin-4-yl)amino]butanoate

HRID 221563Notes

Reaction equation

HRID 221563 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH:15]([CH3:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>C(#N)C.[Pt]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH:15]([CH3:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 67157227Ethyl 3-[(3-nitroquinolin-4-yl)amino]butanoate

Product 1

HCID 67156698Ethyl 3-[(3-aminoquinolin-4-yl)amino]butanoateYield 101.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A Parr vessel was charged with a solution of ethyl 3-[(3-nitroquinolin-4-yl)amino]butanoate (11.5 g, 37.9 mmol) in acetonitrile (150 mL) followed by 5% platinum on carbon (1.2 g). The mixture was placed under hydrogen pressure overnight and then filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure and further dried under high vacuum to provide 10.5 g of ethyl 3-[(3-aminoquinolin-4-yl)amino]butanoate as a sticky, yellow solid.

Workup

  1. custompressure overnight
  2. filtrationfiltered through a layer of CELITE filter agent
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-f89a0bc398ff4a88be80f50c59566600
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

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