Stannous Chloride → HCID 68621262, compound

HRID 407162Notes

Reaction equation

HRID 407162 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[NH:7][N:6]=1)=[O:4].Cl[Sn]Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:10]2[CH:9]=[C:8]3[C:13]([C:5]([C:3]([NH:2][CH3:1])=[O:4])=[N:6][NH:7]3)=[CH:12][CH:11]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 68622096HCID 68622096, compound

Product 1

HCID 68621262HCID 68621262, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of N-methyl-6-(4-nitrophenyl)-1H-indazole-3-carboxamide (154 mg, 0.52 mmol) in ethanol (10 Ml), was added SnCl2 (588 mg, 2.6 mmol) and the mixture was stirred at 80° C. for 3 h. The mixture was cooled to rt and saturated sodium bicarbonate aqueous solution was added. The organic layer was extracted three times and the combined organaic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was triturated in ethyl acetate and hexane to give 6-(4-aminophenyl)-N-methyl-1H-indazole-3-carboxamide (130 mg).

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionThe organic layer was extracted three times
  3. dry with materialthe combined organaic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated in ethyl acetate

Sources & evidence

ORD record
ord-e05080ed612244bf9d8dcab0565d3efd
Source dataset
uspto-grants-2014_06
Patent number
US08754209B2

Reaction notes

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