Stannous Chloride → 5-Fluoroquinolin-8-amine

HRID 513402Notes

Reaction equation

HRID 513402 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Sn](Cl)Cl>Cl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 1539725-Fluoro-8-nitroquinoline2×

Product 1

HCID 445582645-Fluoroquinolin-8-amineYield 106.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

In a similar fashion using route 1 general procedure 4, 5-fluoro-8-nitroquinoline (Intermediate 38) (500 mg, 2.60 mmol), tin (II) chloride (1.48 mg, 7.80 mmol) and 6N HCl (4 drops) gave the title compound (450 mg, >100% crude) which was used in the next step without purification. The structure was confirmed by 1H NMR.

Sources & evidence

ORD record
ord-298ae85fea2e40198d3e3363f146e7b2
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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