Stannous chloride dihydrate → HCID 178508055, compound

HRID 132022Notes

Reaction equation

HRID 132022 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[C:14]([N+:15]([O-])=O)=[CH:13][NH:12][N:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.O.[Sn](Cl)Cl>C(O)C>[C:1]1([NH:7][C:8]([C:10]2[C:14]([NH2:15])=[CH:13][NH:12][N:11]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 178521932HCID 178521932, compound

Product 1

HCID 178508055HCID 178508055, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Nitro-1H-pyrazole-3-carboxylic acid phenylamide (100 mg; 0.43 mmol) was dissolved in ethanol (5 ml), treated with tin (II) chloride dihydrate (500 mg; 2.15 mmol) then heated at reflux overnight. The reaction mixture was cooled and evaporated. The residue was partitioned between ethyl acetate and brine, and the ethyl acetate layer was separated, dried (MgSO4), filtered and evaporated. The crude product was purified by flash column chromatography eluting with 1:1 ethyl acetate /petroleum ether then 5% methanol/dichloromethane. Evaporation of product containing fractions followed by preparative LC/MS gave 15 mg of the product as an off white solid. (LC/MS: Rt 1.40, [M+H]+202.95).

Workup

  1. temperaturethen heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. customevaporated
  5. customThe residue was partitioned between ethyl acetate and brine
  6. customthe ethyl acetate layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude product was purified by flash column chromatography
  11. washeluting with 1:1 ethyl acetate /petroleum ether
  12. customEvaporation of product
  13. additioncontaining fractions

Sources & evidence

ORD record
ord-1b95b025cda74a52a990aa90fc712c82
Source dataset
uspto-grants-2008_06
Patent number
US07385059B2

Reaction notes

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