Stannous Chloride → HCID 68183356, compound

HRID 513403Notes

Reaction equation

HRID 513403 reaction equation
[Cl:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([N+:13]([O-])=O)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Sn](Cl)Cl>Cl>[Cl:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([NH2:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 68183092HCID 68183092, compound2×

Product 1

HCID 68183356HCID 68183356, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

In a similar fashion using route 1 general procedure 4, 5-chloro-6-methyl-8-nitroquinoline (Intermediate 39) (300 mg, 1.35 mmol), tin (II) chloride (760 mg, 4.05 mmol) and 6N HCl (4 drops) gave the title compound (160 mg, 62%) after purification by column chromatography with n-hexane/EtOAc (9:1) as the eluent.

Sources & evidence

ORD record
ord-ae44dfe3568c4ddb86105d73fd83da73
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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