Ammonia → Ethyl 3-(pyridin-2-ylamino)propanoate
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]([O:12][CH2:13][CH3:14])(=[O:11])[CH:9]=[CH2:10].Cl.N>C(OCC)(=O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][CH2:10][CH2:9][C:8]([O:12][CH2:13][CH3:14])=[O:11]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 97.5 °C
Procedure
A mixture of 2-aminopyridine (100 g) and ethyl acrylate (234 g) was heated to 95-100° C. and then stirred for 75 hours at the same temperature. After completion of the reaction, the reaction mixture was cooled to 25-35° C. Ethyl acetate was added to the reaction mixture and treating the reaction mixture with hydrochloric acid followed by ammonia. Both the organic and aqueous layers were separated, the organic layer was washed with sodium chloride solution and then distilled off the solvent completely from the organic layer to get title compound as a residue. The obtained residue was isolated from pet.ether to provide crude title compound. The obtained compound was further purified by column chromatography using pet.ether and ethyl acetate. The obtained pure compound was further recrystallized using pet.ether. Yield: 75 g; MP: 52-54° C.
Workup
- customAfter completion of the reaction
- temperaturethe reaction mixture was cooled to 25-35° C
- customBoth the organic and aqueous layers were separated
- washthe organic layer was washed with sodium chloride solution
- distillationdistilled off the solvent completely from the organic layer
Sources & evidence
- ORD record
- ord-54a9ec4b8e48455eaeb52c511a091220
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273030B2
Reaction notes
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