Phosphorus oxychloride → 3-Amino-5-morpholinopicolinonitrile
Reaction equation
[NH2:1][C:2]1[C:3]([C:14]([NH2:16])=O)=[N:4][CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[NH2:1][C:2]1[C:3]([C:14]#[N:16])=[N:4][CH:5]=[C:6]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of 3-amino-5-morpholinopicolinamide (0.35 g, 1.57 mmol) in acetonitrile (10 mL) was treated with phosphorus oxychloride (0.29 mL, 3.15 mmol). The reaction was heated at reflux for 1 h. After this time the reaction was cooled to rt and evaporated in vacuo. The residue was dissolved in Et2O (10 mL) and treated with 4.0M HCl in dioxane (0.2 mL). The resulting solid was filtered and dried under vacuum to give 3-amino-5-morpholinopicolinonitrile. Mass Spectrum (ESI) m/e=205.2 (M+1).