Stannous Chloride → 8-Quinolinamine, 4-(trifluoromethyl)-

HRID 513735Notes

Reaction equation

HRID 513735 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2[C:14]([F:17])([F:16])[F:15])([O-])=O.Cl[Sn]Cl>Cl.CCO>[F:17][C:14]([F:15])([F:16])[C:9]1[C:8]2[C:13](=[C:4]([NH2:1])[CH:5]=[CH:6][CH:7]=2)[N:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 681832068-Nitro-4-trifluoromethyl-quinoline

Product 1

HCID 681832048-Quinolinamine, 4-(trifluoromethyl)-Yield 89%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 2 general procedure 4, 8-nitro-4-trifluoromethyl-quinoline 468 (900 mg, 4.13 mmol), SnCl2 (3.12 g, 16.5 mmol), 6N HCl (2 drops) and EtOH (20 ml) at 85° C. for 3 h gave the title compound (700 mg, 89%) which was used in the next step without further purification.

Workup

  1. customat 85° C.
  2. customfor 3 h

Sources & evidence

ORD record
ord-3bc4b273e9c84307acfff241f4a43ef5
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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