Stannous Chloride → 5-Methoxyquinolin-8-amine

HRID 513418Notes

Reaction equation

HRID 513418 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.[Sn](Cl)Cl>Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 5207735-Methoxy-8-nitroquinoline2×

Product 1

HCID 7771105-Methoxyquinolin-8-amineYield 91.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

In a similar fashion using route 2 general procedure 4, 5-methoxy-8-nitroquinoline (Intermediate 66) (550 mg, 2.69 mmol), tin (II) chloride (1.53 mg, 8.07 mmol) and 6 N HCl (3 drops) gave the title compound (430 mg, 91%).

Sources & evidence

ORD record
ord-5da22061bd244ef689f22dbeac1baa0a
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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