Potassium Carbonate → 2-Methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carbonitrile
Reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:10])[CH2:5][C:6]=1[C:7]([NH2:9])=O.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[NH:3][C:4](=[O:10])[CH2:5][C:6]=1[C:7]#[N:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 0.9 g (4.6 mmol) of 2-methyl-5-oxo-4,5-dihydropyrrole-3-carboxamide, 1.4 g (9.2 mmol) of phosphorus oxychloride and 0.9 g (6.4 mmol) of potassium carbonate in 50 ml of acetone was refluxed for 6 h. The mixture was then concentrated and the resulting residue was chromatographed over silica gel (mobile phase: cyclohexane:ethyl acetate 10:1 to 1:1). This gave 0.15 g (19% of theory) of the desired product (IR: 2220 cm−1).
Workup
- temperaturewas refluxed for 6 h
- concentrationThe mixture was then concentrated
- customthe resulting residue was chromatographed over silica gel (mobile phase: cyclohexane:ethyl acetate 10:1 to 1:1)
Sources & evidence
- ORD record
- ord-433840dc73f74032bb157ec18fb6c4c0
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06548451B1
Reaction notes
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