1-[(3-Nitroquinolin-4-ylamino)methyl]cyclohexanol → 1-[(3-Aminoquinolin-4-ylamino)methyl]cyclohexanol

HRID 44756Notes

Reaction equation

HRID 44756 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:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>[Pt].C(OCC)(=O)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:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 574578081-[(3-Nitroquinolin-4-ylamino)methyl]cyclohexanol

Product 1

HCID 574578251-[(3-Aminoquinolin-4-ylamino)methyl]cyclohexanol

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[(3-nitroquinolin-4-ylamino)methyl]cyclohexanol (10.0 g, 33.2 mmol), 5% platinum on carbon (1.0 g), and ethyl acetate (140 mL) was placed under hydrogen pressure (40 psi, 2.8×105 Pa) for 2.5 hours. The reaction mixture was filtered through a layer of CELITE filter aid and the filter cake was rinsed with ethyl acetate (100 mL). The filtrate was concentrated under reduced pressure to provide 1-[(3-aminoquinolin-4-ylamino)methyl]cyclohexanol as an orange gooey solid.

Workup

  1. customfor 2.5 hours
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was rinsed with ethyl acetate (100 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a600964fddd74d25b9e9553fb1a408cf
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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