Calcium Chloride → 5-Amino-3-chloropyridine-2-carbonitrile

HRID 501571Notes

Reaction equation

HRID 501571 reaction equation
[Cl:1][C:2]1[C:3]([C:11]#[N:12])=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[Cl-].[Ca+2].[Cl-]>CCO.[Fe]>[NH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([C:11]#[N:12])=[N:4][CH:5]=1

Participants

5

Reactant 2

HCID 5284359Calcium ChlorideHCID 218754953-Chloro-5-nitropicolinonitrile

Product 1

HCID 218750995-Amino-3-chloropyridine-2-carbonitrileYield 44.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of Compound 44C (0.35 g, 1.9 mmol) in 90% EtOH (10 mL) was added calcium chloride (0.06 g, 0.55 mmol), followed by iron powder (0.56 g, 10 mmol). The resulting mixture was stirred at rt overnight, then filtered through a pad of Celite®, the pad washed with EtOAc, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography using 10% Et2O/CH2Cl2 to give a light-brown solid (0.13 g, 43%). 1H NMR (CDCl3) 7.02 (br s, 2H), 7.28 (d, J=2.2 Hz, 1H), 8.16 (d, J=2.2 Hz, 1H); LC/MS m/z=154 [M+H]+.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. washthe pad washed with EtOAc
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-32df2a62d6ee43df80254bf884bb87f2
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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