Stannous Chloride → 8-Aminoquinoline-5-carbonitrile

HRID 513738Notes

Reaction equation

HRID 513738 reaction equation
[N+:1]([C:4]1[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]([C:14]#[N:15])=[CH:6][CH:5]=1)([O-])=O.Cl[Sn]Cl>Cl.CCO>[NH2:1][C:4]1[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]([C:14]#[N:15])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 681834208-Nitroquinoline-5-carbonitrile

Product 1

HCID 681833618-Aminoquinoline-5-carbonitrileYield 86.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 19 general procedure 29, 8-nitroquinoline-5-carbonitrile 471 (350 mg, 1.7 mmol), SnCl2 (1.3 g, 7.0 mmol), 6N HCl (4 drops) and EtOH (10 ml) gave the title compound (250 mg, 86%) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-a15db445fa89492ebebd978bc81edd05
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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