Stannous Chloride → 5-(Benzyloxy)quinolin-8-amine

HRID 513799Notes

Reaction equation

HRID 513799 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl>CCO>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 681832585-Benzyloxy-8-nitro-quinoline

Product 1

HCID 434495875-(Benzyloxy)quinolin-8-amineYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar fashion using route 19 general procedure 29, 5-benzyloxy-8-nitro-quinoline 564 (572 mg, 2.04 mmol), SnCl2 (1.84 g, 8.16 mmol), and EtOH (15 ml) gave the title compound (336 mg, 66%) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-3c58f6813a8a46d683181b3daf2f4b99
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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