HCID 68580149, compound → Methyl 5-cyano-1H-pyrrole-2-carboxylate
Reaction equation
[C:1]([C:3]1[N:7](O)[C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)#[N:2]>O.CO>[C:1]([C:3]1[NH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)#[N:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
A 20% solution of TiCl3 (25 ml, 32 mmol) in water was added to a solution of methyl 5-cyano-1-hydroxy-1H-pyrrole-2-carboxylate (Intermediate 128, 2.55 g, 15 mmol) in MeOH. The reaction was heated to an external temperature of 70° C. for 3 hours. The reaction mixture was concentrated to remove MeOH and the residue was partitioned with EtOAc and water. The organic portion was dried with MgSO4 and concentrated to an orange oil.
Workup
- concentrationThe reaction mixture was concentrated
- customto remove MeOH
- customthe residue was partitioned with EtOAc and water
- dry with materialThe organic portion was dried with MgSO4
- concentrationconcentrated to an orange oil
Sources & evidence
- ORD record
- ord-1c0b0f87e7834a4985c918d9047022d9
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709503B2
Reaction notes
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