Stannous Chloride → HCID 20088007, compound

HRID 275368Notes

Reaction equation

HRID 275368 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:6]([CH:8]=1)[NH2:7].[N:18]([O-])=O.[Na+].Cl[Sn]Cl>Cl.O>[Cl:1][C:2]1[CH:8]=[C:6]2[C:5]([C:9]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[N:18][NH:7]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 223994921493244-95-3HCID 23668193Sodium Nitrite

Product 1

HCID 20088007HCID 20088007, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

To solution of 5-chloro-2-(4-fluorobenzoyl)aniline (5 g) in 6M aqueous HCl (25 ml) was added a solution of NaNO2 (2.5 g) in water (5 ml) at 0°-5° C. under stirring during 15 min. After stirring for further 0.5 h at 0° C. a solution of SnCl2 (20 g) in conc. aqueous HCl (25 ml) was added. The reaction mixture was allowed to heat to room temperature and after 0.5 h the precipitate was filtered off and suspended in 2 N aqueous NaOH. The suspension was filtered and dichloromethane was added to the precipitate. The thus obtained solution was washed with brine and dried (MgSO4). Evaporation of the solvents afforded the title compound (2.5 g) as an oil which was used without further purification. In a corresponding manner the following indazole derivative was prepared: 3-(4-Fluorophenyl)-5-trifluoromethyl-1H-indazole 25b, (oil)

Workup

  1. additionwas added
  2. filtrationwas filtered off
  3. filtrationThe suspension was filtered
  4. additiondichloromethane was added to the precipitate
  5. washThe thus obtained solution was washed with brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvents

Sources & evidence

ORD record
ord-1913f0cdb15f4a8f8f75847c3fae3d06
Source dataset
uspto-grants-1995_02
Patent number
US05393761

Reaction notes

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