Stannous Chloride → 6-Fluoroquinolin-8-amine

HRID 513400Notes

Reaction equation

HRID 513400 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-])=O)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[Sn](Cl)Cl>Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH2:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 154273Quinoline, 6-fluoro-8-nitro-2×

Product 1

HCID 132279926-Fluoroquinolin-8-amineYield 74.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

In a similar fashion using route 1 general procedure 4, 6-fluoro-8-nitroquinoline (Intermediate 36) (1.0 g, 5.41 mmol), tin (II) chloride (3.08 g, 16.2 mmol) and 6N HCl (5 drops) gave the title compound (650 mg, 74%) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-c5a649fabcfb4a2fbff7a40b2275815b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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