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

HRID 1441859Notes

Reaction equation

HRID 1441859 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-674d6e4e8a7a4e4fb75dfa9132ae6037
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Reaction notes

Loading…