Hydrochloric Acid → 4-Chloroquinolin-8-amine

HRID 513731Notes

Reaction equation

HRID 513731 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.Cl[Sn]Cl.Cl>CO>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([NH2:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 6104404-Chloro-8-nitroquinoline

Product 1

HCID 126042744-Chloroquinolin-8-amineYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar fashion using route 2 general procedure 4, 4-chloro-8-nitroquinoline 463 (3.3 g, 15.8 mmol), SnCl2 (15 g, 79.1 mmol), conc. HCl (cat.) and MeOH (100 ml) to give the title compound (2.3 g, 36%) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-b21cad1fcc73415485322d2904f78986
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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