5-Aminopyridine-2-carbonitrile → HCID 178510044, compound

HRID 2408129

Reaction equation

HRID 2408129 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[N:10]1([C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=2)[CH:19]=O)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N:10]1([C:16]2[CH:17]=[C:18](/[CH:19]=[N:1]/[C:2]3[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=3)[CH:21]=[CH:22][CH:23]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 38713955-Aminopyridine-2-carbonitrileHCID 71645843-Morpholinobenzaldehyde

Product 1

HCID 178510044HCID 178510044, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

The mixture solution of 5-amino-pyridine-2-carbonitrile (9.3 g, 78.4 mmol), 3-morpholin-4-yl-benzaldehyde (15.0 g, 78.4 mmol) and p-toluenesulfonic acid (271.8 mg, 1.4 mmol) in toluene (150 mL) was heated to reflux for 12 h. Then the reaction mixture was cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 5-{[1-(3-morpholin-4-yl-phenyl)-meth-(E)-ylidene]-amino}-pyridine-2-carbonitrile (22.9 g, quant.) as a light yellow solid: MS (ESI) M+1=293.0.

Workup

  1. temperatureto reflux for 12 h
  2. customThe solvent was removed in vacuo
  3. washthe residue was washed with ether

Sources & evidence

ORD record
ord-c9d7d888639e442fab511ab3e82ecc93
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Linked notes

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