Stannous Chloride → 6-Ethoxyquinolin-8-amine

HRID 513399Notes

Reaction equation

HRID 513399 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([N+:14]([O-])=O)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2].[Sn](Cl)Cl>Cl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([NH2:14])[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 167725846-Ethoxy-8-nitroquinoline2×

Product 1

HCID 196093906-Ethoxyquinolin-8-amineYield 90.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

In a similar fashion using route 1 general procedure 4, 6-ethoxy-8-nitroquinoline (Intermediate 35) (900 mg, 4.12 mmol), tin (II) chloride (2.4 g, 12.4 mmol) and 6 N HCl (10 drops) gave the title compound (700 mg, 90%) which was used in the next step without purification.

Sources & evidence

ORD record
ord-91a61343ff3e4467ac0fedd488f87839
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…