1-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclobutanol → 1-{[(3-Aminoquinolin-4-yl)amino]methyl}cyclobutanol

HRID 44707Notes

Reaction equation

HRID 44707 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]1([OH:20])[CH2:19][CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>CCO.[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]1([OH:20])[CH2:19][CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 574578111-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclobutanol

Product 1

HCID 574578121-{[(3-Aminoquinolin-4-yl)amino]methyl}cyclobutanolYield 100.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclobutanol (6.32 g, 23.1 mmol) and 20% palladium hydroxide on carbon (0.60 g) in EtOH (100 mL) was hydrogenated overnight on a Parr apparatus at 40 psi (2.8×105 Pa). The mixture was filtered through CELITE filter agent, which was rinsed several times with EtOH, and the filtrate was concentrated to provide 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclobutanol as a pale yellow solid (5.66 g). The solid was concentrated from toluene and chloroform to remove ethanol before using directly in the next reaction.

Workup

  1. filtrationThe mixture was filtered through CELITE
  2. filtrationfilter agent, which
  3. washwas rinsed several times with EtOH
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a53e3dc001e44a21851e1825d4086b1c
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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