Stannous Chloride → HCID 22462531, compound

HRID 1936716Notes

Reaction equation

HRID 1936716 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:8]2[C:9]3[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:10]=3[S:11][CH:12]=2)=[CH:4][CH2:3]1.[Sn](Cl)Cl>C(O)C.Cl>[NH2:17][C:15]1[CH:14]=[CH:13][C:10]2[S:11][CH:12]=[C:8]([C:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH:4]=3)[C:9]=2[CH:16]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 22462551HCID 22462551, compound

Product 1

HCID 22462531HCID 22462531, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A stirred solution of 3-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-5-nitrobenzo[b]thiophene (D13, 470 mg, 1.7 mmole) in ethanol (35 ml) at 60° C. under argon was treated over 5 minutes with a solution of tin (II) chloride (2.0 g, 10.5 mmole) in concentrated HCl acid (4 ml) and the mixture then heated at reflux for 1.5 hours. The reaction mixture was allowed to cool and the precipitate filtered off, washed with ethanol and dried. This was then shaken well with 10% Na2CO3 solution (50 ml) and dichloromethane (100 ml), and the organic layer separated, dried (Na2SO4) and concentrated in vacuo to afford the title compound as a yellow oil (310 mg, 75%).

Workup

  1. temperaturethe mixture then heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureto cool
  4. filtrationthe precipitate filtered off
  5. washwashed with ethanol
  6. customdried
  7. customthe organic layer separated
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0e66299a0e444508b59e841afb309fc
Source dataset
uspto-grants-2002_05
Patent number
US06391891B1

Reaction notes

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