Phosphorus oxychloride → 3-Amino-5-morpholinopicolinonitrile

HRID 1431255Notes

Reaction equation

HRID 1431255 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]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 596313413-Amino-5-morpholinopicolinamide

Product 1

HCID 596312623-Amino-5-morpholinopicolinonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 h
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in Et2O (10 mL)
  5. additiontreated with 4.0M HCl in dioxane (0.2 mL)
  6. filtrationThe resulting solid was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-f3d7308b25604fb2848e703a88694e44
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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