2-Methyl-6-nitroquinoline → 2-Methylquinolin-6-amine

HRID 2302026Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-])=O)[CH:8]=2)[N:3]=1>[OH-].[OH-].[Pd+2].C(OCC)(=O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:12])[CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-methyl-6-nitroquinoline (1.00 g, 5.31 mmol) and Pearlman's catalyst [palladium dihydroxide on activated charcoal (˜20% palladium); 0.10 g] in ethyl acetate (40 mL) was stirred under hydrogen gas (1 atm) at 60° C. for 1.5 h. The reaction mixture was filtered and the filtrate was rotary evaporated. This provided 0.81 g (96%) of 2-methyl-6-aminoquinoline as a yellow solid.

Workup

filtrationThe reaction mixture was filtered

Sources & evidence

ORD record: ord-76de3994568e441fa875744c61b0592c
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06429207B1

Reaction notes

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