4-{[(3-nitroquinolin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol → 4-[(3-Aminoquinolin-4-ylamino)methyl]tetrahydropyran-4-ol

HRID 1363551Notes

Reaction equation

HRID 1363551 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][O:19][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:22])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 575153954-{[(3-nitroquinolin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol

Product 1

HCID 574578244-[(3-Aminoquinolin-4-ylamino)methyl]tetrahydropyran-4-olYield 94%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-{[(3-nitroquinolin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol (9.00 g, 29.7 mmol) and 5% platinum on carbon (0.90 g) in acetonitrile (180 mL) was hydrogenated according to the method described in Part D of Example 9 to yield 4-{[(3-aminoquinolin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol as a brown solid (7.60 g, 94%).

Sources & evidence

ORD record
ord-3af7d828459f425d81730ef24e3e1e21
Source dataset
uspto-grants-2011_02
Patent number
US07884207B2

Reaction notes

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