Ethanol → 3-Amino-5-(3-methyl(2-pyridyl))pyridine-2-carboxamide

HRID 968607Notes

Reaction equation

HRID 968607 reaction equation
[CH3:1][C:2]1[C:3]([C:8]2[CH:9]=[C:10]([N+:16]([O-])=O)[C:11]([C:14]#[N:15])=[N:12][CH:13]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl-].[Ca+2].[Cl-].C([OH:24])C>O.[Fe]>[NH2:16][C:10]1[C:11]([C:14]([NH2:15])=[O:24])=[N:12][CH:13]=[C:8]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 220302915-(3-Methyl(2-pyridyl))-3-nitropyridine-2-carbonitrile

Product 1

HCID 220304133-Amino-5-(3-methyl(2-pyridyl))pyridine-2-carboxamideYield 94%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Heat a solution of 5-(3-methyl(2-pyridyl))-3-nitropyridine-2-carbonitrile (1 g, 4.1 mmol), iron (2.3 g, 40 mmol) and calcium chloride (560 mg, 5 mmol) in ethanol (15 mL) and water (4 mL) to reflux for 1 hour. Cool the mixture, filter through Celite and wash with ethyl acetate. Evaporate the filtrate and re-dissolve the residue in ethyl acetate, wash with water and then with brine, dry (MgSO4) and evaporate to obtain the title compound as a pale yellow solid (880 mg, 94%).

Workup

  1. temperatureto reflux for 1 hour
  2. temperatureCool the mixture
  3. filtrationfilter through Celite
  4. washwash with ethyl acetate
  5. customEvaporate the filtrate
  6. dissolutionre-dissolve the residue in ethyl acetate
  7. washwash with water
  8. dry with materialwith brine, dry (MgSO4)
  9. customevaporate

Sources & evidence

ORD record
ord-f80f6e3923a848ee99759ab1a1cf4c67
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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