Stannous Chloride → HCID 67023933, compound

HRID 450739Notes

Reaction equation

HRID 450739 reaction equation
[N+:1]([C:4]1[CH:16]=[C:15]2[C:7]([C:8]3[CH2:9][CH2:10][N:11]([CH2:20][CH2:21][CH3:22])[CH2:12][C:13]=3[N:14]2C(=O)C)=[CH:6][CH:5]=1)([O-])=O.[Sn](Cl)Cl>CO>[CH2:20]([N:11]1[CH2:10][CH2:9][C:8]2[C:7]3[C:15](=[CH:16][C:4]([NH2:1])=[CH:5][CH:6]=3)[NH:14][C:13]=2[CH2:12]1)[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 67024029HCID 67024029, compound

Product 1

HCID 67023933HCID 67023933, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-(7-nitro-2-propyl-1,2,3,4-tetrahydro-beta-carbolin-9-yl)-ethanone (1.2 g, 2.79 mmol, 70% purity) in methanol (50 ml) was added tin dichloride (5.03 g, 22.3 mmol) and the reaction mixture was refluxed for 3 h. The solvent was removed, the residue treated with 1 N aqueous sodium hydroxide and ethyl acetate, filtered through celite, the phases separated and the aqueous phase extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered, and evaporated to dryness to yield 700 mg of crude product. The crude product was purified with silica gel chromatography with ethyl acetate/methanol (95:5) as eluent to give the desired product (300 mg, 45% yield).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 h
  2. customThe solvent was removed
  3. additionthe residue treated with 1 N aqueous sodium hydroxide and ethyl acetate
  4. filtrationfiltered through celite
  5. customthe phases separated
  6. extractionthe aqueous phase extracted twice with ethyl acetate
  7. dry with materialThe combined organic phases were dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customto yield 700 mg of crude product
  11. customThe crude product was purified with silica gel chromatography with ethyl acetate/methanol (95:5) as eluent

Sources & evidence

ORD record
ord-ba36ed9bd28549b298d98d80973eb7cf
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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