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

HRID 44792Notes

Reaction equation

HRID 44792 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>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

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclohexanol (15.0 g, 49.8 mmol) in ethyl acetate (225 mL) in a Parr vessel was purged with nitrogen; 5% platinum on carbon (1.5 g) was added. The reaction was placed under hydrogen pressure (35 psi, 2.4×105 Pa) for 3.5 hours and then filtered through a layer of CELITE filter agent. The filter cake was washed with ethyl acetate (100 mL), and the filtrate was concentrated under reduced pressure to provide 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclohexanol as a yellow solid.

Workup

  1. customwas purged with nitrogen
  2. addition5% platinum on carbon (1.5 g) was added
  3. customfor 3.5 hours
  4. filtrationfiltered through a layer of CELITE filter agent
  5. washThe filter cake was washed with ethyl acetate (100 mL)
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e84d4bafc38e4ceaa66f15439b558a9a
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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