Water → 4-{[(6-Chloropyridin-3-yl)methyl]amino}furan-2(5H)-one

HRID 425746Notes

Reaction equation

HRID 425746 reaction equation
O.[Cl:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[CH2:11]1[C:16](=[O:17])[O:15][CH2:14][C:12]1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:12]2[CH2:14][O:15][C:16](=[O:17])[CH:11]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 521261Tetronic acidHCID 70209275-(Aminomethyl)-2-chloropyridine

Product 1

HCID 598435524-{[(6-Chloropyridin-3-yl)methyl]amino}furan-2(5H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

On a water separator, 5.00 g (35.1 mmol) of 1-(6-chloropyridin-3-yl)methylamine, 3.51 g (35.1 mmol) of tetronic acid and 20 mg (0.12 mmol) of 4-toluenesulphonic acid in 200 ml of toluene are heated under reflux for 24 hours. The reaction mixture is concentrated, and the residue that remains is then purified by column chromatography on silica gel (silica gel 60—Merck, particle size: 0.04 to 0.063 mm) using the mobile phase ethyl acetate. This gives 4.96 g (63% of theory) of 4-[[(6-chloropyridin-3-yl)methyl]amino]furan-2(5H)-one, which can be used for subsequent reactions.

Workup

  1. temperatureunder reflux for 24 hours
  2. concentrationThe reaction mixture is concentrated
  3. customthe residue that remains is then purified by column chromatography on silica gel (silica gel 60—Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-21974145ea454afa8e82c23b85423699
Source dataset
uspto-grants-2012_01
Patent number
US08106211B2

Reaction notes

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