Stannous Chloride → 8-Amino-5-morpholinoquinoline

HRID 513813Notes

Reaction equation

HRID 513813 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[N:12]3)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[Sn]Cl>CCO>[N:1]1([C:7]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[N:12]3)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 31356775-Morpholin-4-yl-8-nitro-quinoline

Product 1

HCID 145011628-Amino-5-morpholinoquinolineYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar fashion using route 19 general procedure 29, 5-morpholin-4-yl-8-nitro-quinoline 580 (200 mg, 0.77 mmol), SnCl2 (696 mg, 3.09 mmol) and EtOH (5 ml) gave the title compound (154 mg, 87%) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-db868241d5c44a93bec2bb8ebe9094c2
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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