Stannous chloride dihydrate → 3-Amino-5-bromopyridine-2-carboxamide

HRID 1374165Notes

Reaction equation

HRID 1374165 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[OH2:13].O.[Sn](Cl)Cl>CO>[NH2:10][C:4]1[C:5]([C:8]([NH2:9])=[O:13])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 210758623-Amino-5-bromopyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5-bromo-3-nitropyridine-2-carbonitrile (4.71 g, 20.7 mmol) in MeOH (319 mL) under N2 was added tin(II) chloride dihydrate (27.97 g, 123.9 mmol). The reaction was heated to 40° C. for 40 minutes, concentrated in vacuo, and azeotroped with toluene. The residue was dissolved in ethyl acetate, and 10% aqueous sodium bicarbonate was added till the solution was basic. The aqueous layer was extracted 3× with CHCl3 and the combined organics were dried over Na2SO4, filtered and concentrated under vacuum to provide 3-amino-5-bromopyridine-2-carboxamide that gave a mass ion (ES+) of 218.2 for M+H+(81Br).

Workup

  1. concentrationconcentrated in vacuo
  2. customazeotroped with toluene
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. addition10% aqueous sodium bicarbonate was added till the solution
  5. extractionThe aqueous layer was extracted 3× with CHCl3
  6. dry with materialthe combined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a9dd9df294b34c4f8537d444a72cb3df
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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