Stannous Chloride → 6-(Trifluoromethoxy)quinolin-8-amine

HRID 513398Notes

Reaction equation

HRID 513398 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([O:15][C:16]([F:19])([F:18])[F:17])[CH:7]=[C:8]2[C:13]=1[NH:12][C:11](=O)[CH:10]=[CH:9]2)([O-])=O.[Sn](Cl)Cl>Cl>[F:19][C:16]([F:17])([F:18])[O:15][C:6]1[CH:7]=[C:8]2[C:13](=[C:4]([NH2:1])[CH:5]=1)[N:12]=[CH:11][CH:10]=[CH:9]2

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 866697558-Nitro-6-(trifluoromethoxy)quinolone2×

Product 1

HCID 681830016-(Trifluoromethoxy)quinolin-8-amineYield 84.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

In a similar fashion using route 1 general procedure 4, 8-nitro-6-(trifluoromethoxy)quinolone (Intermediate 34) (1.1 g, 4.26 mmol), tin (II) chloride (2.42 g, 12.8 mmol) and 6 N HCl (13 drops) gave the title compound (820 mg, 84%) which was used in the next step without purification.

Sources & evidence

ORD record
ord-21318f5fd3394da6869a56505f1ad65e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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