8-{[(3-Nitroquinolin-4-yl)amino]methyl}-1,4-dioxaspiro[4.5]decan-8-ol → 8-{[(3-Aminoquinolin-4-yl)amino]methyl}-1,4-dioxaspiro[4,5]decan-8-ol

HRID 1469252Notes

Reaction equation

HRID 1469252 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:26])[CH2:25][CH2:24][C:19]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>[Pt].C(#N)C>[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:26])[CH2:25][CH2:24][C:19]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 669191558-{[(3-Nitroquinolin-4-yl)amino]methyl}-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 669191388-{[(3-Aminoquinolin-4-yl)amino]methyl}-1,4-dioxaspiro[4,5]decan-8-olYield 99.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 8-{[(3-nitroquinolin-4-yl)amino]methyl}-1,4-dioxaspiro[4.5]decan-8-ol (12.0 g, 33.4 mmol) and 5% platinum on carbon (1.2 g) in acetonitrile (120 mL) was hydrogenated at 50 psi (3.5×105 Pa) for 4 hours (h) on a Parr apparatus. The reaction mixture was filtered through CELITE filter agent with dichloromethane and ethanol. The filtrate was concentrated to give 8-{[(3-aminoquinolin-4-yl)amino]methyl}-1,4-dioxaspiro[4.5]decan-8-ol as a orange solid (10.9 g, 99%).

Workup

  1. filtrationThe reaction mixture was filtered through CELITE
  2. filtrationfilter agent with dichloromethane and ethanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-fd8e6d9dd920400fa03f79ba7061cce1
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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