6-Methoxy-3-nitroquinoline → 6-Methoxyquinolin-3-amine

HRID 1043782Notes

Reaction equation

HRID 1043782 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([N+:13]([O-])=O)=[CH:6]2.[H][H]>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([NH2:13])=[CH:6]2

Participants

5

Reactant 2

HCID 15193946-Methoxy-3-nitroquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 5999396-Methoxyquinolin-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-methoxy-3-nitroquinoline (Magnus, P. et al., J. Am. Chem. Soc. 119, 5591, 1997; 0.17 g, 0.83 mmol) and Pd/C (10%, 80 mg) in EtOAc (15 mL) was hydrogenated with a hydrogen balloon to give 6-methoxyquinolin-3-amine in quantitative yield. LC/MS (m/z): 175.1 (MH+), Rt 1.54 minutes.

Sources & evidence

ORD record
ord-728ab622c747430cb7707ec65bb325dd
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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