Stannous Chloride → HCID 67284195, compound

HRID 541079Notes

Reaction equation

HRID 541079 reaction equation
Cl[Sn]Cl.[CH2:4]([C:12]1[N:13]([CH2:24][CH3:25])[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([N+:21]([O-])=O)=[CH:16][CH:15]=2)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([O-])(O)=O.[Na+]>C1COCC1.O>[CH2:4]([C:12]1[N:13]([CH2:24][CH3:25])[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([NH2:21])=[CH:16][CH:15]=2)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 67285354HCID 67285354, compound

Product 1

HCID 67284195HCID 67284195, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

SnCl2 (1.2 g, 6.3 mmol) was added to a solution of 2-phenethyl-1-ethyl-5-nitro-1H-indole (0.17 g, 0.57 mmol) in THF (50 ml). The mixture was kept under stirring at 70° C. overnight. After cooling, the mixture was poured in H2O, neutralized with NaHCO3, and extracted with ethyl acetate (3×50 ml). After evaporation of the solvent under reduced pressure, the solid was purified on a chromatographic column using CHCl3 as eluent to give 2-phenethyl-1-ethyl-1H-indol-5-amine.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. customAfter evaporation of the solvent under reduced pressure
  4. customthe solid was purified on a chromatographic column

Sources & evidence

ORD record
ord-d3e49ee8224e47388aaaa9186a3797df
Source dataset
uspto-grants-2014_10
Patent number
US08871948B2

Reaction notes

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