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

HRID 2110481Notes

Reaction equation

HRID 2110481 reaction equation
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([N+:10]([O-])=O)=[CH:5][N:4]=1)#[N:2].[Cl-].[Ca+2].[Cl-]>C(O)C.[Fe]>[NH2:10][C:6]1[CH:7]=[C:8]([CH3:9])[C:3]([C:1]#[N:2])=[N:4][CH:5]=1

Participants

5

Reactant 2

HCID 5284359Calcium ChlorideHCID 124040403-Methyl-5-nitropicolinonitrile

Product 1

HCID 218645665-Amino-3-methylpyridine-2-carbonitrileYield 81%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

2-Cyano-3-methyl-5-nitropyridine (0.2 g, 1.23 mmol) was dissolved in 6 mL of 90% ethanol and calcium chloride (0.07 g, 0.64 mmol) was added followed by iron powder (0.62 g, 11.1 mmol, 325 Mesh). The heterogeneous mixture was stirred for one h. The mixture was filtered though Celite and concentrated to give compound 772B (0.13 g, 81%) as a light-brown solid.

Workup

  1. filtrationThe mixture was filtered though Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3d89fcb7e0cc4453a3aa067a1e6cc500
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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