Stannous chloride dihydrate → HCID 67128488, compound

HRID 449914Notes

Reaction equation

HRID 449914 reaction equation
[N:1]([C:4]1[CH:9]=[C:8]([NH:10][C:11](=[O:21])[C:12]2[C:17]([Cl:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=2[Cl:20])[CH:7]=[CH:6][N:5]=1)=[N+]=[N-].O.O.Cl[Sn]Cl>C(O)C>[NH2:1][C:4]1[CH:9]=[C:8]([NH:10][C:11](=[O:21])[C:12]2[C:13]([Cl:20])=[CH:14][C:15]([Cl:19])=[CH:16][C:17]=2[Cl:18])[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 86648957N-(2-azidopyridin-4-yl)-2,4,6-trichlorobenzamide

Product 1

HCID 67128488HCID 67128488, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(2-azidopyridin-4-yl)-2,4,6-trichlorobenzamide (90 mg, 0.26 mmol) in ethanol (5 mL) was added SnCl2.2H2O (300 mg, 1.31 mmol). The mixture was heated at reflux for 1 hour and then cooled to room temperature. The reaction was concentrated under reduced pressure and the residue was diluted with water (10 mL). The mixture was extracted with ethyl acetate (3×5 mL). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure to give N-(2-aminopyridin-4-yl)-2,4,6-trichlorobenzamide (82 mg, yield: 100%). LCMS (ESI) m/z: 316.0 [M+H+].

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. concentrationThe reaction was concentrated under reduced pressure
  4. additionthe residue was diluted with water (10 mL)
  5. extractionThe mixture was extracted with ethyl acetate (3×5 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f409f8f0b8054e70adbd5b16ab8a6bc2
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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