Stannous Chloride → HCID 178438015, compound

HRID 1880402Notes

Reaction equation

HRID 1880402 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Br:9])=[CH:4][C:3]=1[C:10](=O)[CH2:11][CH3:12].[N:14]([O-])=O.[Na+].Cl[Sn]Cl>OS(O)(=O)=O.O>[Br:9][C:5]1[CH:4]=[C:3]2[C:2](=[C:7]([Cl:8])[CH:6]=1)[NH:1][N:14]=[C:10]2[CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 23668193Sodium NitriteHCID 66920482HCID 66920482, compound

Product 1

HCID 178438015HCID 178438015, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

1-(2-Amino-5-bromo-3-chloro-phenyl)-propan-1-one (130.0 mg, 0.50 mmol) dissolved in aqueous 50% H2SO4 (2.5 mL) and NaNO2 (43.1 mg, 0.59 mmol) was slowly added to this mixture at 0° C. The mixture was then stirred at room temperature for 1 hour. SnCl2 2H2O (342.0 mg, 1.48 mmol) was then added, and the mixture was stirred at 0° C. for 1 hour, and then diluted with water. White solid appeared and was collected by filtration and dried to afford 5-bromo-7-chloro-3-ethyl-1H-indazole as a solid (127.0 mg, 98.8%).

Workup

  1. additionwas slowly added to this mixture at 0° C
  2. stirringthe mixture was stirred at 0° C. for 1 hour
  3. filtrationwas collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-552023fa2d6b4707845062ff3fb0642d
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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