Stannous Chloride → 5-Methylquinolin-8-amine

HRID 513396Notes

Reaction equation

HRID 513396 reaction equation
[CH3:1][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>[CH3:1][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 64278395-Methyl-8-nitroquinoline2×

Product 1

HCID 128466255-Methylquinolin-8-amineYield 118.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

In a similar fashion using route 1 general procedure 4, 5-methyl-8-nitroquinoline (Intermediate 32) (950 mg, 5.05 mmol), tin (II) chloride (2.87 g, 15.1 mmol) and 6 N HCl (5 drops) gave the title compound (950 mg, >100% crude) which was used in the next step without purification. The structure was confirmed by 1H NMR.

Sources & evidence

ORD record
ord-5e1443f4b070423888d2b5cf1fb5e649
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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