Stannous Chloride → 7-Methoxyquinolin-8-amine

HRID 513415Notes

Reaction equation

HRID 513415 reaction equation
[CH3:1][O:2][C:3]1[C:12]([N+:13]([O-])=O)=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[Sn](Cl)Cl>Cl>[CH3:1][O:2][C:3]1[C:12]([NH2:13])=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 112064927-METHOXY-8-NITROQUINOLINE2×

Product 1

HCID 128498137-Methoxyquinolin-8-amineYield 71%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

In a similar fashion using route 1 general procedure 4, 7-methoxy-8-nitroquinoline (Intermediate 61) (250 mg, 1.22 mmol), tin (II) chloride (700 mg, 3.67 mmol) and 6N HCl (3 drops) gave the title compound (150 mg, 71%) which was used in the next step without purification.

Sources & evidence

ORD record
ord-8d3c1d62687d403ba18caa0a97ecb183
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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